2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

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361 reactions in Reaxys

2018-08-18 00h:22m:12s (UTC)

H 2N O

1. Query HO

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='118-92-3') AND (IDE.INCHI='RWZYAGGXGHYGMB-UHFFFAOYSA-N') NOT (RX.RXRN=471803))

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O H 2N O

O

HO

O

Rx-ID: 87314 View in Reaxys 1/361 Yield

Conditions & References I.G. Farbenind.; View in Reaxys Reaction Steps: 2 1: ammonium hydroxide / 300 °C 2: sodium hydroxide; bromine; sodium bromate / water / 0 - 70 °C With ammonium hydroxide, sodium bromate, bromine, sodium hydroxide in water Liu, Gang; Qiu, Mingxiang; Sun, Lin; Wen, Quanwu; Xu, Shengguang; Wang, Xuyuan; Wang, Peng; Letters in Organic Chemistry; vol. 13; nb. 1; (2016); p. 44 - 48 View in Reaxys Reaction Steps: 4 1: hydroxylamine hydrochloride; triethylamine / ethanol / 3 h / 95 °C 2: acetone 3: chloroform 4: water; potassium carbonate / acetonitrile / 2 h / 20 °C With hydroxylamine hydrochloride, water, potassium carbonate, triethylamine in ethanol, chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 4 1: hydroxylamine hydrochloride; triethylamine / ethanol / 3 h / 95 °C 2: acetone 3: chloroform 4: water; potassium carbonate / acetonitrile / 2 h / 20 °C With hydroxylamine hydrochloride, water, potassium carbonate, triethylamine in ethanol, chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 4 1: hydroxylamine hydrochloride; triethylamine / ethanol / 3 h / 95 °C 2: acetone 3: chloroform 4: water; potassium carbonate / acetonitrile / 2 h / 20 °C With hydroxylamine hydrochloride, water, potassium carbonate, triethylamine in ethanol, chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 4 1: hydroxylamine hydrochloride; triethylamine / ethanol / 3 h / 95 °C 2: acetone 3: chloroform 4: water; potassium carbonate / acetonitrile / 2 h / 20 °C With hydroxylamine hydrochloride, water, potassium carbonate, triethylamine in ethanol, chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Reaction Steps: 4 1: hydroxylamine hydrochloride; triethylamine / ethanol / 3 h / 95 °C 2: acetone 3: chloroform 4: water; potassium carbonate / acetonitrile / 2 h / 20 °C With hydroxylamine hydrochloride, water, potassium carbonate, triethylamine in ethanol, chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 2 1: ammonium hydroxide / 6.5 h / 40 °C / Cooling with ice 2: sodium hydroxide; sodium hypochlorite / water / 80 °C / Cooling with ice With ammonium hydroxide, sodium hypochlorite, sodium hydroxide in water Patent; Shenyang Pharmaceutical University; Jin Zhe; Hu Chun; Tang Wenping; Wang Danni; Zhang Furong; Zhang Qingguang; Zhang Kaikai; Shao Pengzhu; (13 pag.); CN107793369; (2018); (A) Chinese View in Reaxys Reaction Steps: 2 1: ammonium hydroxide / 6.5 h / 40 °C / Cooling with ice 2: sodium hydroxide; sodium hypochlorite / water / 80 °C / Cooling with ice With ammonium hydroxide, sodium hypochlorite, sodium hydroxide in water Patent; Shenyang Pharmaceutical University; Jin Zhe; Hu Chun; Tang Wenping; Wang Danni; Zhang Furong; Zhang Qingguang; Zhang Kaikai; Shao Pengzhu; (13 pag.); CN107868060; (2018); (A) Chinese View in Reaxys Reaction Steps: 3 1: urea / 0.5 h / 140 °C 2: chlorine / 3 h / 20 °C 3: sodium hydroxide / 1 h / 20 °C With chlorine, urea, sodium hydroxide Patent; Shandong Ju Qiang Chemical Co., Ltd.; Ye Huatian; Wang Tao; Zhang Pengpeng; Liu Qi; (6 pag.); CN108101800; (2018); (A) Chinese View in Reaxys O

H 2N O NH

HO O

Rx-ID: 87547 View in Reaxys 2/361 Yield 85.5 %

Conditions & References With bromine, sodium hydroxide Tang, Yang; Zhang, Siqi; Chang, Yajing; Fan, Dacheng; Agostini, Ariane De; Zhang, Lijuan; Jiang, Tao; Journal of Medicinal Chemistry; vol. 61; nb. 7; (2018); p. 2937 - 2948 View in Reaxys

78.7 %

Stage 1: With bromine, sodium hydroxide in water, Time= 0.0333333h, T= -5 °C , Reflux Stage 2: With hydrogenchloride in water, pH= 4 - 5 Yin, Ruijuan; Zhang, Meng; Hao, Cui; Wang, Wei; Qiu, Peiju; Wan, Shengbiao; Zhang, Lijuan; Jiang, Tao; Chemical Communications; vol. 49; nb. 76; (2013); p. 8516 - 8518 View in Reaxys

78.7 %

1.1 : preparation of anthranilic acid Fitted with mechanical agitation, thermometer 500 ml adding three-necked bottle 54.0g NaOH (1.35mol) dissolved in 54 ml of water to form a solution, adding 150g ice, salt bath cooling to -7 ° C the following, under stirring instillment bromine 11.1 ml

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(0.22mol), temperature control in the -5 ° C the following, is added in batches after dropping 30.0g (0.20mol) phthalimide, subsequently joined 28g (0.70mol) of NaOH 40 ml aqueous solution. Stirring 1h reflux after 2 min, cooling to room temperature, concentrated HCl to adjust pH about 7-8, then glacial acetic acid for adjusting the pH to 4-5, until the precipitation-free, stirring 10 min after filtering, washing 3 times, with 200 ml distilled water recrystallization, placing sleepovers, filtered to obtain brown acicular crystal 22.0g, yield 78.7percent, With bromine, sodium hydroxide in water, Time= 1h, Reflux Patent; Ocean University of China; Jiang, Tao; Yin, ruijuan; Zhang, Li Juan; (38 pag.); CN103497211; (2016); (B) Chinese View in Reaxys Chapman; Stephen; Journal of the Chemical Society; vol. 127; (1925); p. 1794 View in Reaxys Fierz-David,H.E.; Blangey,L.; View in Reaxys With potassium hydroxide, iodosylbenzene Tscherniac; Chemische Berichte; vol. 36; (1903); p. 218 View in Reaxys With sodium hydroxide, sodium hypochlorite, water, man erwaermt auf 80grad, neutralisiert mit Salzsaeure oder Schwefelsaeure und versetzt mit Essigsaeure Patent; Bad. Anilin- u. Sodaf.; DE55988; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 2; p. 546 View in Reaxys With sodium hydroxide, sodium hypobromide Patent; Maumee Devel. Co.; US2653971; (1951) View in Reaxys With potassium hydroxide, potassium hypobromite Hoogewerff; van Dorp; Recueil des Travaux Chimiques des Pays-Bas; vol. 10; (1891); p. 6 View in Reaxys Preparation of Anthranilic Acid Phthalic anhydride (10.0 g) was gradually added to aqueous ammonia (10 mL) with stirring, and dissolved readily with considerable evolution of heat until 300°C. The reactants were cooled, and ground into a powder in a mortar to produce solid phthalic imide. Sodium hydroxide (7.5 g) and freshwater (or seawater) (30 mL) were placed in a 125 mL Erlenmeyer flask. After cooling to 0-5°C, bromine (2.3 mL) was immediately added with stirring for dissolution in an ice bath. Sodium hydroxide (5.5 g) and freshwater or seawater (20 mL) were combined in another 125 mL Erlenmeyer flask and placed in an ice bath. Powdered phthalic imide (6.0 g)was slowly added into the aqueous solution of sodium bromate at a temperature below 0°C. The prepared sodium hydroxide solution was added to the mixture, which was cooled to 0°C. The mixture was placed in a rotary shaking conical bottle at room temperature, and heated to 20-25°C for 15-20min. The mixture was maintained at 20-25°C for 10 min and 25-30°C for 30 min, and phthalic imide was completely dissolved.The mixtures were heated further at 70°C in a water bath for a few minutes. Saturated aqueous sodium hydrogen sulfite (approximately 2 mL) was added to the mixtures, which were filtered after shaking and cooled in an ice bath. Concentrated hydrochloric acid solution (12 mL) was addedto the mixtures with gentle stirring, and glacial acetic acid (6-7 mL) was gradually added to anthranilic acid. After filtration, washing with cold water, recrystallization, and decoloration in hot water, white flaky crystals were obtained. The yield using seawater was 77percent, mp 142-144°C (Literature[6]: Yield 71.7-80.6percent, mp 144-145°C). The synthesis route of anthranilic acid is shown in Scheme 1.

With sodium bromate, bromine, sodium hydroxide in water, T= 0 - 70 °C Liu, Gang; Qiu, Mingxiang; Sun, Lin; Wen, Quanwu; Xu, Shengguang; Wang, Xuyuan; Wang, Peng; Letters in Organic Chemistry; vol. 13; nb. 1; (2016); p. 44 - 48 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O H 2N O

N

Cl

HO

O

Rx-ID: 121764 View in Reaxys 3/361 Yield 96.4 %

Conditions & References 2 :(4) After the reaction was stirred at room temperature for three hours, a solid was collected by filtration, 100 g of water was used to wash the solid, and the mother liquor was added to the next batch of the reaction solution;(5) Put the solid into 1800g liquid caustic soda Stir at room temperature for one hour. The liquid caustic soda was used as a 40percent by weight sodium hydroxide solution;(6) adding hydrochloric acid to the reaction solution to adjust the PH = 3-4, precipitate a lot of solid;(7) Filter and dry the product 535g o-aminobenzoic acid, content 99.3percent, yield 96.4percent;The acetic acid solution used in the process can be applied, and after the application, the yield is improved and the quality is stable. The wastewater after centrifuging the product was light yellow and the COD in the wastewater was 1710.

With sodium hydroxide, Time= 1h, T= 20 °C Patent; Shandong Ju Qiang Chemical Co., Ltd.; Ye Huatian; Wang Tao; Zhang Pengpeng; Liu Qi; (6 pag.); CN108101800; (2018); (A) Chinese View in Reaxys With sodium hydroxide Patent; Hoechster Farbw.; DE133950 View in Reaxys

OH H 2N

O

O

O N

HO

O

Rx-ID: 282904 View in Reaxys 4/361 Yield 99.9 %

Conditions & References With hydrazine in ethanol, Time= 0.166667h, T= 80 °C , Catalytic behavior, chemoselective reaction Cui, Xueliang; Zhang, Qiaolan; Tian, Meng; Dong, Zhengping; New Journal of Chemistry; vol. 41; nb. 18; (2017); p. 10165 - 10173 View in Reaxys

95 %

With hydrazine hydrate in ethanol, Time= 5h, T= 60 °C , Sealed tube, Green chemistry, chemoselective reaction Reddy, P. Linga; Tripathi, Mohit; Arundhathi; Rawat, Diwan S.; Chemistry - An Asian Journal; vol. 12; nb. 7; (2017); p.

785 - 791 View in Reaxys

94 %

Stage 1: in water, acetonitrile, Time= 0.0833333h, T= 20 °C Stage 2: With sodium tetrahydroborate in water, acetonitrile, Time= 0.333333h, T= 20 °C , chemoselective reaction Setamdideh, Davood; Khezri, Behrooz; Mollapour, Manouchehr; Oriental Journal of Chemistry; vol. 27; nb. 3; (2011); p.

991 - 996 View in Reaxys

94 %

With sodium tetrahydroborate, nickel(II) chloride hexahydrate in water, acetonitrile, Time= 0.1h, T= 20 °C , chemoselective reaction Setamdideh, Davood; Khezri, Behrooz; Asian Journal of Chemistry; vol. 22; nb. 7; (2010); p. 5575 - 5580 View in Reaxys

94.5 %

3 : Example 3 S1: In a reactor, 22.5 g of o-nitrobenzoic acid, 250 mL of ethanol and 0.25 g of nano nickel catalyst are sequentially added;S2: At the same time of stirring, hydrogen gas is introduced to replace the air in the reaction system 3-4 times, Control the hydrogen

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

pressure to 1 atmosphere Pressure, stirred at 20 ° C for 6 hours to achieve catalytic hydrogenation;S3: filtering under reduced pressure, washing the filter cake with the same solvent as step S1 to collect the nano-nickel catalyst;S4: the filtrate obtained in step S3 was concentrated under reduced pressure to give a solid, which is the product of anthranilic acid crude product;S5: The resulting crude product was recrystallized from dichloromethane / hexane and dried at room temperature to give 17.5 g of the product in 94.5percent yield.

With hydrogen in ethanol, Time= 6h, T= 20 °C , p= 760.051Torr Patent; Hebei University of Science and Technology; Liu Shouxin; Meng Tianxing; Zhang Zhiwei; Feng Juan; Huang Jing; Li Junzhang; (6 pag.); CN106905173; (2017); (A) Chinese View in Reaxys 92 %

With hydrazine hydrate, zinc in methanol, Time= 0.133333h, T= 20 °C Gowda, Shankare; Gowda, D. Channe; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 1; (2003); p. 180 - 183 View in Reaxys

92 %

A typical procedure for reduction of nitrobenzene to anilinewith NaBH4/additive Ni2B system General procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction,aqueous solution of KOH (2 percent, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 percent yield (0.088 g, Table 2, entry 1).

Stage 1: With nickel boride in water, Time= 0.0833333h, T= 20 °C , Green chemistry Stage 2: With sodium tetrahydroborate in water, Time= 0.166667h, T= 20 °C , Green chemistry Zeynizadeh, Behzad; Zabihzadeh, Mehdi; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1221 - 1226; Art.No: 585 View in Reaxys

91.5%

Hydrogenation Reactions of Nitroarenes General procedure: The nitroarenes were reduced with hydrazine hydratecatalyzed by G-Fe3O4. Typically, 2.0 mmol nitroarene,0.01 g G-Fe3O4 and 4.0 mmol 80percent hydrazine hydrate wereadded in turn into a 50 ml round-bottom flask. The mixturewas stirred at 70 oC for an appropriate time depending uponthe nature of the substrate. Upon completion of the reaction(monitored by TLC), 5 ml of ethanol was added and ahomogeneous solution was obtained. The mixture wascooled to room temperature and the catalyst was filtered offfor recycling tests. The filtrate was concentrated underreduced pressure. The residue was subjected to silica-gelcolumn chromatography using petroleum ether/ethyl acetateas an eluent to give pure product. The products were identifiedby IR and 1H NMR. With hydrazine hydrate, Time= 5h, Reflux, chemoselective reaction Zhang, Hai-Yan; Feng, Cheng; Shang, Ning-Zhao; Gao, Shu-Tao; Wang, Chun; Wang, Zhi; Letters in Organic Chemistry; vol. 10; nb. 1; (2013); p. 17 - 21 View in Reaxys

90 %

With hydrazine glyoxylate, zinc, Time= 0.5h, T= 20 °C Raju; Ragul; Sivasankar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 48; nb. 9; (2009); p.

1315 - 1318 View in Reaxys

90 %

With hydrogen in water, Time= 12h, T= 60 °C , p= 760.051Torr , Green chemistry Yang, Fan; Feng, Andong; Wang, Chunxia; Dong, Sen; Chi, Cheng; Jia, Xilai; Zhang, Liqiang; Li, Yongfeng; RSC Advances; vol. 6; nb. 21; (2016); p. 16911 - 16916 View in Reaxys

90 %

With hydrogen in water, Time= 18h, T= 60 °C , p= 760.051Torr Yang, Fan; Dong, Sen; Wang, Chunxia; Li, Yongfeng; RSC Advances; vol. 6; nb. 58; (2016); p. 52620 - 52626 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

90 %

General Procedure for Reductions: General procedure: Nitro compound or olefin(5 mmol) and hydrogen source (25 mmol) were dissolved inMeOH (10 mL, 0.5 M). After flushing the column with MeOH,the substrate/reagent solution was pumped through the columnat the specified temperature with a flow rate of 0.108 mL/minby using Vapourtec E-series equipment (with a peristalticpump). Alternatively, a syringe pump can be used. The firstcolumn volume was discarded, the second was collected. Thesolvent was evaporated, the residue added to distilled water (20 mL), and extracted with diethyl ether or dichloromethane(3 × 15 mL). The combined organic phases were dried overMgSO4, filtered, and the solvent was removed in vacuo.

With Johnson & Matthey type 440, hydrogen, ammonium formate in methanol, p= 2068.65Torr , Flow reactor Hutchings, Matthew; Wirth, Thomas; Synlett; vol. 27; nb. 12; (2016); p. 1832 - 1835; Art.No: ST-2016-D0074-L View in Reaxys

90 %

With sodium tetrahydroborate in water, Time= 2h, T= 20 °C , Green chemistry Keshipour, Sajjad; Adak, Kamran; RSC Advances; vol. 6; nb. 92; (2016); p. 89407 - 89412 View in Reaxys

86 %

3.1 : Preparation of o-aminobenzoic acid O-nitrobenzoic acid (10.00 g, 59.90 mmol) was dissolved in 1 mol / L dilute hydrochloric acid solution, adjusted to pH 4.0 to 4.5 with sodium hydroxide,Hydrochloric acid-activated iron powder (16.70 g, 299.50 mmol) was added portionwise at room temperature and the solution was brown-black after mechanical stirring at 50 ° C for 2 h. Filtered and washed filter cake twice, combined filtrate, the filtrate with dilute hydrochloric acid to adjust the pH to 4.0 ~ 5.0, a white crystal precipitation, drying white needle-like crystals (7.10g, 86.0percent), melting point 144 ° C ~ 146 ° C. With hydrogenchloride, iron, sodium hydroxide in water, Time= 2h, T= 50 °C , pH= 4 - 4.5 Patent; Xuzhou Medical University; Liu, Yi; Ding, Yan; Luo, Xuan; Guo, Anlei; Hua, Yuzhou; Liu, Li; Huang, Jie; Fang, Tongyong; (15 pag.); CN106243035; (2016); (A) Chinese View in Reaxys

86 %

With sodium tetrahydroborate in water, Time= 1.5h, T= 20 °C , Inert atmosphere Moghaddam, Firouz Matloubi; Ayati, Seyed Ebrahim; Firouzi, Hamid Reza; Hosseini, Seyed Hassan; Pourjavadi, Ali; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3825 View in Reaxys

85.6 %

With sodium tetrahydroborate, nickel dichloride in methanol, Time= 0.5h, T= 20 °C Nose, Atsuko; Kudo, Tadahiro; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 1159 - 1161 View in Reaxys

85 %

With tin, ammonium bromide in methanol, Time= 0.333333h, T= 65 °C Pasha; Jayashankara; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 11; (2004); p.

2464 - 2466 View in Reaxys

80 %

With 10 % Pd-C, hydrazine hydrate in ethanol, Time= 1.5h, T= 0 - 80 °C , Inert atmosphere Osman, Wesseem; Mohamed, Tarek; Sit, Victor Munsing; Vasefi, Maryam S.; Beazely, Michael A.; Rao, Praveen P. N.; Chemical Biology and Drug Design; (2016); p. 710 - 723 View in Reaxys

75 %

With ammonium chloride, aluminium in methanol, Time= 7h, Heating, Reduction Nagaraja; Pasha; Tetrahedron Letters; vol. 40; nb. 44; (1999); p. 7855 - 7856 View in Reaxys

75 %

With ammonium chloride, aluminium in methanol, Time= 1.45h, T= 25 °C , Irradiation, sonication at 35 KHz, Reduction Nagaraja; Pasha; Tetrahedron Letters; vol. 40; nb. 44; (1999); p. 7855 - 7856 View in Reaxys

75 %

Stage 1: With 5% Pd/C, hydrazine hydrate, sodium hydroxide in water, Time= 6h, T= 50 - 60 °C Stage 2: With hydrogenchloride in water, pH= 3 - 4

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Zheng, Chunling; Yuan, Ailin; Zhang, Zhengyu; Shen, Hong; Bai, Shuyuan; Wang, Haibo; Journal of Fluorescence; vol.

23; nb. 4; (2013); p. 785 - 791 View in Reaxys 73 %

4.2 Typical procedure for reduction of nitrobenzene General procedure: Nitrobenzene (0.6mmol), 5wtpercent Pd/C (0.5mmol percent, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50°C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99percent).

With tetrahydroxydiboron, Johnson & Matthey type 440, water in acetonitrile, Time= 24h, T= 50 °C Zhou, Yanmei; Zhou, Haifeng; Liu, Sensheng; Pi, Danwei; Shen, Guanshuo; Tetrahedron; vol. 73; nb. 27-28; (2017); p.

3898 - 3904 View in Reaxys

72 %

Stage 1: With acetic acid, Time= 0.5h, T= 90 °C Stage 2: With iron, Time= 2h Chauhan, Monika; Joshi, Gaurav; Kler, Harveen; Kashyap, Archana; Amrutkar, Suyog M.; Sharma, Praveen; Bhilare, Kiran D.; Chand Banerjee, Uttam; Singh, Sandeep; Kumar, Raj; RSC Advances; vol. 6; nb. 81; (2016); p. 77717 - 77734 View in Reaxys

70 %

With ammonium sulfate, sodium tetrahydroborate in ethanol, Time= 1h, Ambient temperature Gohain, Sujata; Prajapati, Dipak; Sandhu, Jagir S.; Chemistry Letters; nb. 8; (1995); p. 725 - 726 View in Reaxys

65 %

With sulfur, aluminum oxide, sodium hydroxide, Time= 7h, T= 80 °C Niknam, Khodabakhsh; Kiasat, Ali Reza; Kazemi, Foad; Hossieni, Abolghasem; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 6; (2003); p. 1385 - 1389 View in Reaxys

52 %

4.1.2. Typical procedure for the synthesis of 8-Aminoquinoline (4a) General procedure: A 20 mL Schlenk tube was charged with 8-nitroquinoline (1k; 87 mg, 0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4(135 mg, 1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 80 °C for 24 h, then cooled to room temperature and concentrated under reduced pressure. Similar workup to 2a gave a brown solid (4a: 63 mg, 87percent yield).

With tetrahydroxydiboron, copper diacetate in acetonitrile, Time= 24h, T= 80 °C , Schlenk technique, chemoselective reaction Pi, Danwei; Zhou, Haifeng; Zhou, Yanmei; Liu, Qixing; He, Renke; Shen, Guanshuo; Uozumi, Yasuhiro; Tetrahedron; vol. 74; nb. 17; (2018); p. 2121 - 2129 View in Reaxys

50 %

General procedure for reductive cyclization of o-nitrobenzaldehydes to 2,1-benzisoxazoles General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.

With vasicine in ethylene glycol, Time= 48h, T= 80 °C Sharma, Sushila; Kumar, Manoranjan; Bhatt, Vinod; Nayal, Onkar S.; Thakur, Maheshwar S.; Kumar, Neeraj; Singh, Bikram; Sharma, Upendra; Tetrahedron Letters; vol. 57; nb. 45; (2016); p. 5003 - 5008 View in Reaxys

38 %

2-Aminobenzoic acid (5l) General procedure: A round bottom flask equipped with a magnetic stirrer bar was charged with the 2-nitroacylbenzene (1.00 mmol) in EtOAc–MeOH (1:1; 5 mL). SnCl2.H2O (3.00 mmol) was added and the reaction stirred at room temperature overnight.

The reaction was partitioned between DCM (30 mL) and NaHCO3 (20 mL). The aqueous phase was extracted with DCM (3 × 10 mL) and the organic portions combined, washed with H2O (10 mL), saturated aqueous NaCl (10 mL), dried over MgSO4, filtered and reduced in vacuo. The residue was purified by column chromatography (SiO2, hexane/EtOAc) to provide the title compound. General procedure gave the title compound as a yellow solid (51 mg, 38 percent).

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

With tin(II) chloride dihdyrate in methanol, ethyl acetate, Time= 20h, T= 25 °C Chauhan, Jay; Fletcher, Steven; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 4951 - 4954 View in Reaxys With hydrogenchloride, tin Beilstein; Kuhlberg; Justus Liebigs Annalen der Chemie; vol. 163; (1872); p. 126 View in Reaxys With sodium metabisulfite, zinc Goldberger; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 1014 View in Reaxys With sulfuric acid, T= 80 °C , Reduktion Shipley; Calhoun; Canadian Journal of Research, Section B: Chemical Sciences; vol. 13; (1935); p. 123,125, 131 View in Reaxys With acetic anhydride, tin(ll) chloride, anschliessend Hydrolyse de Kiewiet; Stephen; Journal of the Chemical Society; (1931); p. 82 View in Reaxys With tin Isgaryschew; Fioschin; Zhurnal Obshchei Khimii; vol. 24; (1954); p. 766,768; engl. Ausg. S. 773 View in Reaxys With amalgamated zinc-cathodes Isgaryschew; Fioschin; Zhurnal Obshchei Khimii; vol. 24; (1954); p. 766,768; engl. Ausg. S. 773 View in Reaxys With sodium hydroxide, ethanol, zinc Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 289; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 450 View in Reaxys With platinum(IV) oxide, ethanol, T= 25 - 30 °C , p= 1900 - 2280Torr , Hydrogenation Adams; Cohen; Rees; Journal of the American Chemical Society; vol. 49; (1927); p. 1095 View in Reaxys With hydrogenchloride, titanium(III) chloride Fluerschheim; Holmes; Journal of the Chemical Society; (1928); p. 451 View in Reaxys With sodium hydroxide, T= 25 °C , electrochemical reduction, Yield given Stutts, K. J.; Scortichini, C. L.; Repucci, C. M.; Journal of Organic Chemistry; vol. 54; nb. 15; (1989); p. 3740 - 3744 View in Reaxys With ammonium formate, zinc in methanol, T= 20 °C Gowda, D. Channe; Mahesh, B.; Gowda, Shankare; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 40; nb. 1; (2001); p. 75 - 77 View in Reaxys 85 %Spectr. With [Pd(HBOADO)]Cl2, hydrogen in water, N,N-dimethyl-formamide, Time= 0.283333h Shanker; Rohini; Shravankumar; Reddy, P. Muralidhar; Ho, Yen-Peng; Ravinder; Journal of the Indian Chemical Society; vol. 86; nb. 2; (2009); p. 153 - 161 View in Reaxys

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With sodium tetrahydroborate in methanol, T= 20 - 40 °C Zeng, Zhao-Sen; He, Qiu-Qin; Liang, Yong-Hong; Feng, Xiao-Qing; Chen, Fen-Er; Clercq, Erik De; Balzarini, Jan; Pannecouque, Christophe; Bioorganic and Medicinal Chemistry; vol. 18; nb. 14; (2010); p. 5039 - 5047 View in Reaxys With hydrogen in methanol, Time= 1h, T= 20 °C , p= 750.075Torr , chemoselective reaction Pandarus, Valerica; Ciriminna, Rosaria; Beland, Francois; Pagliaro, Mario; Advanced Synthesis and Catalysis; vol. 353; nb. 8; (2011); p. 1306 - 1316 View in Reaxys With hydrogen in methanol, T= 30 °C , p= 596Torr Velua, Udayakumar; Stanislaus, Alexander; Virupaiah, Gayathri; Shivakumaraiah; Patil, Kashinath Rangu; Balasubramanian, Viswanathan; Journal of Chemical Research; vol. 35; nb. 2; (2011); p. 112 - 115 View in Reaxys With formic acid, [RuCl3(pHPB)3(OH2)]*2H2O in methanol, N,N-dimethyl-formamide, Time= 15h, Reflux Krishnamurthy; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 41; nb. 6; (2011); p.

590 - 597 View in Reaxys With hydrogen in methanol, T= 30 °C , p= 760.051Torr , Kinetics Alexander; Udayakumar; Nagaraju; Gayathri; Transition Metal Chemistry; vol. 35; nb. 2; (2010); p. 247 - 251 View in Reaxys With oxalic acid, titanium(IV) oxide in acetonitrile, Time= 2h, T= 24.84 °C , p= 760.051Torr , Inert atmosphere, UV-irradiation Imamura, Kazuya; Hashimoto, Keiji; Kominami, Hiroshi; Chemical Communications; vol. 48; nb. 36; (2012); p. 4356 4358 View in Reaxys With carbon dioxide, hydrogen, Time= 0.166667h, T= 50 °C , p= 18751.9 - 90009Torr , Supercritical conditions Chatterjee, Maya; Chatterjee, Abhijit; Kawanami, Hajime; Ishizaka, Takayuki; Suzuki, Toshishige; Suzuki, Akira; Advanced Synthesis and Catalysis; vol. 354; nb. 10; (2012); p. 2009 - 2018 View in Reaxys With hydrogen in methanol, T= 30 °C , p= 760.051Torr Alexander; Udayakumar; Gayathri; Transition Metal Chemistry; vol. 37; nb. 1; (2012); p. 1 - 6 View in Reaxys With 10% palladium on activated charcoal, hydrogen Dong, Kui-Kui; Zhou, Hua-Hong; Guo, A-Rong; Chen, Tian; Wang, Yu-Liang; Asian Journal of Chemistry; vol. 25; nb. 2; (2013); p. 1039 - 1042 View in Reaxys With 10% palladium on activated carbon; Degussa type in tetrahydrofuran, Time= 24h, T= 20 °C Yu, Yongguo; Wu, Jianbo; Lei, Fan; Chen, Lei; Wan, Weili; Hai, Li; Guan, Mei; Wu, Yong; Letters in Drug Design and Discovery; vol. 10; nb. 4; (2013); p. 369 - 373 View in Reaxys 99 %Chromat.

With hydrogen in ethanol, Time= 5h, T= 20 °C , p= 750.075Torr , Schlenk technique Li, Zelong; Li, Jinlei; Liu, Jianhua; Zhao, Zelun; Xia, Chungu; Li, Fuwei; ChemCatChem; vol. 6; nb. 5; (2014); p. 1333 1339 View in Reaxys With sodium tetrahydroborate in water, T= 20 °C , Kinetics, Reagent/catalyst Jana, Subhra; Das, Sankar; RSC Advances; vol. 4; nb. 65; (2014); p. 34435 - 34442

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys 4.1 General General procedure: Three kinds of commercial TiO2 samples were used as photocatalyst, i.e., P 25 (Degussa), ST-01 (Ishihara), and MT-150A (Tayca). Bare TiO2 powder (50mg) was suspended in a mixture of acetonitrile (Wako Pure Chemical Industries, Osaka) and water (5cm3) containing NS (50μmol, Sigma–Aldrich Japan, Tokyo) and oxalic acid (200μmol, Wako Pure Chemical Industries, Osaka) in a test tube. The tube was sealed with a rubber septum and then photoirradiated at a wavelength >300nm by a high-pressure mercury arc (Eiko-sha, 400W) under argon (Ar) with magnetic stirring at 298K. After the reaction, the gas phase was analyzed by a gas chromatograph (Shimadzu, GC-8A equipped with MS-5A columns). After the suspension had been filtered to remove the particles, the amounts of NS and product(s) were determined by high-performance liquid chromatography (Jasco, UV-2075Plus detector, PU-2089Plus pump, equipped with an Inertsil ODS-3 column, eluent: aqueous sodium borate buffer/acetonitrile=50:50, flow rate: 0.5cm3min−1 at room temperature) and GC–MS (GC-17A, GCMS-QP5050 (Shimadzu); column: DB-1, 0.25mm, 30m (J&W)).

With oxalic acid, titanium(IV) oxide in water, acetonitrile, Time= 2h, T= 24.84 °C , p= 760.051Torr , Inert atmosphere, UVirradiation, Sealed tube, chemoselective reaction Imamura, Kazuya; Nakanishi, Kousuke; Hashimoto, Keiji; Kominami, Hiroshi; Tetrahedron; vol. 70; nb. 36; (2014); p.

6134 - 6139 View in Reaxys With hydrogen in ethyl acetate, Time= 1h, T= 20 °C , p= 760.051Torr , Schlenk technique Shen, Kui; Chen, Liang; Long, Jilan; Zhong, Wei; Li, Yingwei; ACS Catalysis; vol. 5; nb. 9; (2015); p. 5264 - 5271 View in Reaxys General procedure General procedure: A mixture of nitrobenzenes 1 (1mmol) and Zn (215mg, 3.3mmol) in solvent of HOAc–H2O (2.5mL, v/ v=2:3) in a flask was stirred at room temperature until the starting nitrobenzenes were consumed completely (monitored by TLC analysis). NaNO2 (1.1mmol) saturated solution was added dropwise at 0–5°C in an ice-water bath followed by adding a 1.5mmol of NaN3 saturated solution. Then the ice-water bath was removed and the reaction proceeded at room temperature.

After 2h, terminal alkynes 2 (1.2mmol), CuI (0.05mmol) and DMSO (1.5mL) were added to the above system at room temperature. After 5h, the mixture was treated with H2O (15mL) and extracted with EtOAc (3×15mL) and the combined organic layer was washed with brine (3×5mL), dried over Na2SO4 and concentrated under reduced pressure to afford a crude product. Purification by column chromatography on silica gel afforded the desired 1,4-disubstitued 1,2,3-triazol 3.

With acetic acid, zinc in water, T= 20 °C Zhao, Fen; Chen, Zhen; Xie, Kai; Yang, Rui; Jiang, Yu-Bo; Chinese Chemical Letters; vol. 27; nb. 1; (2016); p. 109 - 113 View in Reaxys Nitroarenes reduction reaction General procedure: The substrate (0.5 mmol), NiPd/MIL-101 catalyst (0.023g, Pd 0.2 molpercent), and ethyl acetate (4 mL) were added to a Schlenk tube, and the mixture was vigorously stirred with an affixed hydrogenation balloon at room temperature. Following the reaction, the solid catalyst was removed from the solution by filtration and washed with ethyl acetate. The product yields were determined by gas chromatography-mass spectrometry (GC/MS, Shimadzu GCMS- QP5050A) with a 0.25 mm × 30 mDB-WAX capillary column. Parameters were as follows: initialoven temperature, 100 °C, 1 min; ramp, 20 °C/min; final temperature, 280 °C; final time, 5 min.

With hydrogen in ethyl acetate, Time= 2h, T= 30 °C , p= 750.075Torr , Schlenk technique, Catalytic behavior, chemoselective reaction Jian, Siping; Li, Yingwei; Chinese Journal of Catalysis; vol. 37; nb. 1; (2016); p. 91 - 97 View in Reaxys 99 %Chromat.

2.3. General procedure for hydrogenation General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L nhexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

With hydrogen in methanol, Time= 2h, T= 100 °C , p= 7500.75Torr , Autoclave, chemoselective reaction Wang, Xi; Li, Yingwei; Journal of Molecular Catalysis A: Chemical; vol. 420; (2016); p. 56 - 65 View in Reaxys With hydrogen in ethanol, Time= 0.5h, T= 140 °C , p= 3750.38Torr , Autoclave, Green chemistry, chemoselective reaction Tang, Bo; Song, Wei-Chao; Yang, En-Cui; Zhao, Xiao-Jun; RSC Advances; vol. 7; nb. 3; (2017); p. 1531 - 1539 View in Reaxys With sodium tetrahydroborate in water, Time= 0.0833333h, Reagent/catalyst Nazir, Roshan; Fageria, Pragati; Basu, Mrinmoyee; Gangopadhyay, Subhashis; Pande, Surojit; New Journal of Chemistry; vol. 41; nb. 18; (2017); p. 9658 - 9667 View in Reaxys

H 2N

NH O

O

O

HO

Rx-ID: 548055 View in Reaxys 5/361 Yield 84 %

Conditions & References With dihydrogen peroxide, sodium hydroxide in water, Time= 3h, T= 30 - 40 °C Wu, Gaochan; Gao, Yun; Kang, Dongwei; Huang, Boshi; Huo, Zhipeng; Liu, Huiqing; Poongavanam, Vasanthanathan; Zhan, Peng; Liu, Xinyong; MedChemComm; vol. 9; nb. 1; (2018); p. 149 - 159 View in Reaxys With ammonium hydroxide, dihydrogen peroxide Jacini; Gazzetta Chimica Italiana; vol. 72; (1942); p. 510,514 View in Reaxys With potassium hydroxide Isbell; Henze; Journal of the American Chemical Society; vol. 66; (1944); p. 2096 View in Reaxys With sodium hydroxide, dihydrogen peroxide, T= 10 - 15 °C Patent; Kalle and Co.; DE375616; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 448 View in Reaxys 5-octyl Anthranilic Acid A mixture of the isatin (1.5 g, 5.8 mmol) and 1.5M sodium hydroxide (13 ml) was warmed to 50° C. The heat was removed and a solution of 35percent aqueous hydrogen peroxide (1.5 ml) was added, at a rate that maintained the temperature at 50-55° C. The reaction was then allowed to cool and stirred at room temperature for 30 min.

Acidification to pH 2 with concentrated hydrochloric acid caused the product to precipitate.

The liquid was decanted off, the solid being washed with water.

The solid was partitioned between water and dichloromethane, the organic phase being washed with brine, dried (MgSO4) and concentrated to give the desired anthranilic acid (1.4 g, 5.6 mmol).

No further purification was required: δ(400 MHz, CDCl3) 0.81 (3H, t, J 6.6, Me), 1.20-1.23 (10H, m, 5*CH2), 1.49 (2H, br.s, ArCH2CH2), 2.41-2.44 (2H, m, ArCH2), 6.55 (1H, d, J 8.3, ArH), 7.09 (1H, d, J 8.3, ArH), 7.65 (1H, s, ArH); m/z (ES+) 250 (MH+).

With sodium hydroxide, dihydrogen peroxide Patent; Hodson, Harold Francis; Downham, Robert; Mitchell, Timothy John; Carr, Beverley Jane; Dunk, Christopher Robert; Palmer, Richard Michael John; US2003/27821; (2003); (A1) English

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys With sodium hydroxide, dihydrogen peroxide, Time= 2h, T= 20 °C Seong, Churl Min; Park, Woo Kyu; Park, Chul Min; Kong, Jae Yang; Park, No Sang; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 2; (2008); p. 738 - 743 View in Reaxys With dihydrogen peroxide, sodium hydroxide in water Pokhodylo, Nazariy T.; Matiychuk, Vasyl S.; Journal of Heterocyclic Chemistry; vol. 47; nb. 2; (2010); p. 415 - 420 View in Reaxys H 2N

H 2N

O

O

O

HO

Rx-ID: 5251722 View in Reaxys 6/361 Yield 97.4 %

Conditions & References With sodium hydroxide in water, Time= 12h, T= 20 °C Zhu, Jie; Yang, Hongyu; Chen, Yao; Lin, Hongzhi; Li, Qi; Mo, Jun; Bian, Yaoyao; Pei, Yuqiong; Sun, Haopeng; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 33; nb. 1; (2018); p. 496 - 506 View in Reaxys

95 %

1.5 : 5) Preparation of o-aminobenzoic acid WeighedO-aminobenzoic acidMethyl ester(12.1 g, 80 mmol)250mL round bottomIn the flask,50 mL of saturated aqueous sodium hydroxide solution was added,After heating in a 105 ° C oil bath for 2.5 h.Reaction is completed,Cooled to room temperature,At this point the solution was orange,With 1.0mol / L dilute hydrochloric acid to adjust the system pH to 3-4 or so,At this time a small amount of white solid precipitation;The reaction system was added with glacial acetic acid,A large number of white solid precipitation, suction filtration,Filter cake washed,Dried in vacuo to give 10.4 g of a white solid in 95percent yield. M.p.

144-146 ° C (literature value: 144-146 ° C) (Carlier P.R., Han Y.F., ChowE.S. Biorg. Med. Chem. 1999, 7, 351-357). The above data confirm that the compound is o-aminobenzoic acid.

With sodium hydroxide in water, Time= 2.5h, T= 105 °C Patent; National Chi Nan University; Chen, Heru; Wang, Rikang; Zhou, Jiaqiang; Zhang, Lei; (19 pag.); CN106565675; (2017); (A) Chinese View in Reaxys

95 %

1.1 : (1) Preparation of anthranilic acid: Methyl anthranilate (12.1 g, 80 mmol) was weighed into a 250 mL round bottom flask and 50 mL of saturated aqueous sodium hydroxide was added and the reaction heated in an oil bath at 105 ° C for 2.5 h. The reaction is completed, cooled to room temperature, the solution was orange yellow, with 1.0mol / L dilute hydrochloric acid system pH value to 3-4 or so, a small amount of white solid precipitation; to the reaction system was added dropwise glacial acetic acid, a large number A white solid precipitated, suction filtered, washed with water and dried in vacuo to give a white solid 10.4g, yield 95percent.

With sodium hydroxide in water, Time= 2.5h, T= 105 °C Patent; Jinan University; Chen Heru; Zhang Lei; Zhang Chao; (20 pag.); CN107522691; (2017); (A) Chinese View in Reaxys

92 %

With NaSiO(CH3)3 in tetrahydrofuran, Time= 30h, T= 20 °C Lovric, Marija; Cepanec, Ivica; Litvic, Mladen; Bartolincic, Anamarija; Vinkovic, Vladimir; Croatica Chemica Acta; vol.

80; nb. 1; (2007); p. 109 - 115 View in Reaxys With Carbonate buffer in acetonitrile, T= 29 °C , pH= 9.8, Hydrolysis, Kinetics Bastide; Badon; Cambon; Vega; Pesticide Science; vol. 40; nb. 4; (1994); p. 293 - 297 View in Reaxys With hydrogenchloride in water, T= 5 °C , Kinetics, Temperature, Concentration

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yu, Zhiqun; Dong, Hei; Xie, Xiaoxuan; Liu, Jiming; Su, Weike; Organic Process Research and Development; vol. 20; nb. 12; (2016); p. 2116 - 2123 View in Reaxys With sodium hydroxide in water, Time= 3h, T= 60 °C Ma, Fang; Du, Hongtao; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 118 - 127 View in Reaxys 10.7 g

1.1 : O-aminobenzoic acid methyl ester hydrolysis to produce o-aminobenzoic acid weighing 30g (0.2 mol) anthranilic acid methyl ester and 16g sodium hydroxide, the consumer O-aminobenzoic acid is poured into 200 ml of the single port flask, add 50 ml tetrahydrofuran, to prepare the anthranilic acid methyl ester solution, then 100 ml of distilled water to dissolve the weighing of sodium hydroxide, into the sodium hydroxide aqueous solution, the sodium hydroxide aqueous solution is added to the single-port flask with the anthranilic acid methyl ester in the mixed solution. The mixed reaction solution in 68 °C under heating, condensing and refluxing, the reaction 3h. After the end of the to be reacted, cooling to room temperature, takes the response solution for removing turns on lathe steams the meter tetrahydrofuran solvent in the reaction system, then the ice HCl to adjust the pH value to under neutral (ph7), a large amount of white precipitate generated. Filtering to collect precipitation, first is washed with distilled water for 2 - 3 times, then the ethanol solution is washed 2 - 3 times, the washed precipitate in 60 °C lower vacuum drying overnight, to obtain 10.7g white solid powder, i.e. O-aminobenzoic acid.

With water, sodium hydroxide in tetrahydrofuran, Time= 3h, T= 68 °C Patent; Chongqing University of Technology; Yang, Chaolong; Su, Yan; Li, Youbing; Gao, Bao; Zhang, Qiang; (24 pag.); CN106432305; (2017); (A) Chinese View in Reaxys

O H 2N

H 2N

O

O HO

OH

Rx-ID: 47794527 View in Reaxys 7/361 Yield 55.07 %

Conditions & References 1 : Example 1 Into an eggplant-shaped flask was added sodium hydroxide 2.0 g (0.05 mol), a small amount of water was added until the sodium hydroxide was completely dissolved, an intermediate 2-carbamoylbenzoic acid 1.65 g (0.01 mol) was added, and a small amount of water was added. Make it completely dissolved. Under ice-cooling, 22.5 g (0.015 mol) of a 10percent sodium hypochlorite solution was added dropwise. After the addition was completed, the mixture was stirred overnight in an ice bath and stirred at 80° C. for an additional 4 hours. The pH was adjusted to 2 by cooling and a large amount of brick-red solids precipitated. , suction filtration, drying, to obtain the intermediate 2-aminobenzoic acid, yield 55.07percent, With sodium hypochlorite, sodium hydroxide in water, T= 80 °C , Cooling with ice Patent; Shenyang Pharmaceutical University; Jin Zhe; Hu Chun; Tang Wenping; Wang Danni; Zhang Furong; Zhang Qingguang; Zhang Kaikai; Shao Pengzhu; (13 pag.); CN107793369; (2018); (A) Chinese View in Reaxys

55.07 %

1 :Into an eggplant-shaped flask was added sodium hydroxide 2.0 g (0.05 mol), a small amount of water was added until the sodium hydroxide was completely dissolved, an intermediate 2-carbamoylbenzoic acid 1.65 g (0.01 mol) was added, and a small amount of water was added. Make it completely dissolved.Under ice-cooling, 22.5 g (0.015 mol) of a 10percent sodium hypochlorite solution was added dropwise. After the addition was complete, the mixture was stirred overnight in an ice bath and stirred at 80° C. for another 4 h.Cooling, adjusting the pH value to 2, a large number of brick red solids precipitated, suction filtration, and drying to obtain the intermediate 2-aminobenzoic acid, yield 55.07percent, With sodium hypochlorite, sodium hydroxide in water, T= 80 °C , Cooling with ice Patent; Shenyang Pharmaceutical University; Jin Zhe; Hu Chun; Tang Wenping; Wang Danni; Zhang Furong; Zhang Qingguang; Zhang Kaikai; Shao Pengzhu; (13 pag.); CN107868060; (2018); (A) Chinese View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N

N O

O

NH

NH 2

HO

Rx-ID: 47808243 View in Reaxys 8/361 Yield

Conditions & References

88 %

With potassium hydroxide in methanol, Time= 24h, T= 120 °C , Sealed tube Yu, Lin; Chen, Xiang; Liu, Da; Hu, Liang; Yu, Yongqi; Huang, Hang; Tan, Ze; Gui, Qingwen; Advanced Synthesis and Catalysis; vol. 360; nb. 7; (2018); p. 1346 - 1351 View in Reaxys

H 2N O

O

NH N

HO

Rx-ID: 47808250 View in Reaxys 9/361 Yield

Conditions & References Reaction Steps: 2 1: sodium azide; nickel dichloride; potassium carbonate; tetrabutylammonium acetate; water / dimethyl sulfoxide / 24 h / 100 °C / Schlenk technique; Inert atmosphere 2: potassium hydroxide / methanol / 24 h / 120 °C / Sealed tube With sodium azide, water, tetrabutylammonium acetate, potassium carbonate, potassium hydroxide, nickel dichloride in methanol, dimethyl sulfoxide Yu, Lin; Chen, Xiang; Liu, Da; Hu, Liang; Yu, Yongqi; Huang, Hang; Tan, Ze; Gui, Qingwen; Advanced Synthesis and Catalysis; vol. 360; nb. 7; (2018); p. 1346 - 1351 View in Reaxys

O H 2N O

N H 2H

N

O

HO

Rx-ID: 48296626 View in Reaxys 10/361 Yield

Conditions & References Reaction Steps: 2 1: diphenylmethanone O-pivaloyl oxime; copper (I) acetate; dipotassium hydrogenphosphate / dimethyl sulfoxide / 2 h / 90 °C / Inert atmosphere 2: potassium hydroxide / ethanol / 16 h / 80 °C With dipotassium hydrogenphosphate, diphenylmethanone O-pivaloyl oxime, copper (I) acetate, potassium hydroxide in ethanol, dimethyl sulfoxide

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Xu, Lin-Lin; Wang, Xing; Ma, Biao; Yin, Ming-Xing; Lin, Hai-Xia; Dai, Hui-Xiong; Yu, Jin-Quan; Chemical Science; vol.

9; nb. 23; (2018); p. 5160 - 5164 View in Reaxys

O H 2N O

N H

N

HO

O

Rx-ID: 48296664 View in Reaxys 11/361 Yield

Conditions & References Reaction Steps: 3 1: copper (I) acetate; dipotassium hydrogenphosphate / dimethyl sulfoxide / 8 h / 90 °C / Inert atmosphere 2: hydrogenchloride; water / 0.33 h / 20 °C 3: potassium hydroxide / ethanol / 16 h / 80 °C With hydrogenchloride, dipotassium hydrogenphosphate, water, copper (I) acetate, potassium hydroxide in ethanol, dimethyl sulfoxide Xu, Lin-Lin; Wang, Xing; Ma, Biao; Yin, Ming-Xing; Lin, Hai-Xia; Dai, Hui-Xiong; Yu, Jin-Quan; Chemical Science; vol.

9; nb. 23; (2018); p. 5160 - 5164 View in Reaxys

O H 2N

H 2N

O

N H

N NH 2

N

HO

O

O

Rx-ID: 48296690 View in Reaxys 12/361 Yield

Conditions & References

81 %, 74 %

With potassium hydroxide in ethanol, Time= 16h, T= 80 °C Xu, Lin-Lin; Wang, Xing; Ma, Biao; Yin, Ming-Xing; Lin, Hai-Xia; Dai, Hui-Xiong; Yu, Jin-Quan; Chemical Science; vol.

9; nb. 23; (2018); p. 5160 - 5164 View in Reaxys

O H 2N

N H

O

N

O

N HO

Rx-ID: 48296735 View in Reaxys 13/361 Yield

Conditions & References Reaction Steps: 2 1: hydrogenchloride; water / 0.33 h / 20 °C

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

2: potassium hydroxide / ethanol / 16 h / 80 °C With hydrogenchloride, water, potassium hydroxide in ethanol Xu, Lin-Lin; Wang, Xing; Ma, Biao; Yin, Ming-Xing; Lin, Hai-Xia; Dai, Hui-Xiong; Yu, Jin-Quan; Chemical Science; vol.

9; nb. 23; (2018); p. 5160 - 5164 View in Reaxys H 2N

H 2N O

HO

HO

Rx-ID: 38124203 View in Reaxys 14/361 Yield 95 %

Conditions & References With C30H24AgBr4N8 (1+)*AgBr2 (1-), potassium hydroxide in 1,2-dimethoxyethane, Time= 24h, T= 60 °C , Molecular sieve, Schlenk technique Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 16; nb. 13; (2014); p. 3428 - 3431 View in Reaxys

99 %Chromat.

With [RuH(CO)(py-NP)(PPh3)2]Cl, water, sodium hydroxide, Time= 6h, T= 110 °C Sarbajna, Abir; Dutta, Indranil; Daw, Prosenjit; Dinda, Shrabani; Rahaman, S. M. Wahidur; Sarkar, Abheek; Bera, Jitendra K.; ACS Catalysis; vol. 7; nb. 4; (2017); p. 2786 - 2790 View in Reaxys O H 2N O

N

OH

HO

O

Rx-ID: 44994110 View in Reaxys 15/361 Yield

Conditions & References Reaction Steps: 3 1: acetone 2: chloroform 3: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 3 1: acetone 2: chloroform 3: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 3 1: acetone 2: chloroform 3: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603

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View in Reaxys Reaction Steps: 3 1: acetone 2: chloroform 3: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 3 1: acetone 2: chloroform 3: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetone, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

O

N

O

OH

O

H 2N

O

O

O

HO

Rx-ID: 44994118 View in Reaxys 16/361 Yield

Conditions & References

Ca. 20 %Chromat.

With water, potassium carbonate in acetonitrile, Time= 2h, T= 20 °C Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

O

N

O

O

O

H 2N

O

O O

O

H N

O

OH

OH N

O

H HO

Rx-ID: 44994142 View in Reaxys 17/361 Yield

Conditions & References General procedure of Fmoc formation; Fmoc-Phe-OH

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General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.

With water, potassium carbonate in acetonitrile, Time= 2h, T= 20 °C , Overall yield = 80 percent Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

O O

N

O

O

O

H 2N

N H

O

HO NH 2

O

O

NH 2 O

O

HO

Rx-ID: 44994146 View in Reaxys 18/361 Yield

Conditions & References General procedure of Fmoc formation; Fmoc-Phe-OH General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.

With water, potassium carbonate in acetonitrile, Time= 2h, T= 20 °C , Overall yield = 67 percent Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

O

N

O

O HO

OH

O

O

O

H 2N

O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

O

OH HN

H 2N

O

HO

O

O HO

Rx-ID: 44994149 View in Reaxys 19/361 Yield

Conditions & References General procedure of Fmoc formation; Fmoc-Phe-OH General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.

With water, potassium carbonate in acetonitrile, Time= 2h, T= 20 °C , Overall yield = 80 percent Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

O

O

OH

HO O

N

O

HN

O

O

O

O

O

OH

HO

H 2N

O

O

O

HO

NH 2

Rx-ID: 44994151 View in Reaxys 20/361 Yield

Conditions & References General procedure of Fmoc formation; Fmoc-Phe-OH General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.

With water, potassium carbonate in acetonitrile, Time= 2h, T= 20 °C , Overall yield = 82 percent Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys

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O

H 2N HN HO

O

N

HO O

Rx-ID: 44994185 View in Reaxys 21/361 Yield

Conditions & References Reaction Steps: 2 1: chloroform 2: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 2 1: chloroform 2: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 2 1: chloroform 2: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 2 1: chloroform 2: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys Reaction Steps: 2 1: chloroform 2: water; potassium carbonate / acetonitrile / 2 h / 20 °C With water, potassium carbonate in chloroform, acetonitrile Yoshino, Ryo; Tokairin, Yoshinori; Kikuchi, Mari; Konno, Hiroyuki; Tetrahedron Letters; vol. 58; nb. 16; (2017); p. 1600 1603 View in Reaxys O

H 2N O O N

HO O

Rx-ID: 8706108 View in Reaxys 22/361

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Yield

Conditions & References

50 mg

With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, Time= 168000h, T= 20 °C Sammelson; Olmstead; Haddadin; Kurth; Journal of Organic Chemistry; vol. 65; nb. 26; (2000); p. 9265 - 9267 View in Reaxys Reaction Steps: 2 1: tin dichloride; hydrochloric acid 2: NaOH-solution With hydrogenchloride, sodium hydroxide, tin(ll) chloride Friedlaender; Henriques; Chemische Berichte; vol. 15; (1882); p. 2105 View in Reaxys Reaction Steps: 2 1.1: potassium permanganate / acetone; water / 1 h 2.1: acetic acid / 0.5 h / 90 °C 2.2: 2 h With potassium permanganate, acetic acid in water, acetone Chauhan, Monika; Joshi, Gaurav; Kler, Harveen; Kashyap, Archana; Amrutkar, Suyog M.; Sharma, Praveen; Bhilare, Kiran D.; Chand Banerjee, Uttam; Singh, Sandeep; Kumar, Raj; RSC Advances; vol. 6; nb. 81; (2016); p. 77717 - 77734 View in Reaxys H 2N

H 2N

H 2N

O

O

HO

Rx-ID: 20846245 View in Reaxys 23/361 Yield

Conditions & References

99 %

11 :in 250 ml round bottom flask was added anthranilamide XXVII16. 32 g, 0.12 Moore hydroxide Potassium 33.6 g, 0.60 mole, was added 60 ml of water and 60 ml of ethanol, stirred and heated under reflux for 6 hours, ethanol was distilled off, ice-bath cooling, with concentrated hydrochloric acid, and pH = 7, further addition of glacial acetic acid was acidified at pH = 3, large amount of solid precipitation, filtration as a white solid, drying in anthranilate XXVII113 09 g, yield 99percent; With potassium hydroxide in ethanol, water, Time= 6h, Reflux Patent; Jiangxi Tianren Ecology Co., Ltd.; Nankai University; Chen, Xiaoyan; Liu, Xiping; Fan, Zhijin; Liang, Xiaowen; Li, Yuedong; Mao, Wutao; Li, Juanjuan; Wang, Dun; Wang, Shuhua; Zhou, Lifeng; Ji, Xiaotian; HUA, XUEWEN; (23 pag.); CN102942565; (2016); (B) Chinese View in Reaxys Reaction Steps: 3 2: 40 percent / KOH / methanol / Ambient temperature 3: 45 percent / aq. NaOH / 16 h / Heating With potassium hydroxide, sodium hydroxide in methanol Ranganathan, Darshan; Farooqui, Firdous; Bhattacharyya, Diphti; Mehrotra, Sanjiv; Kesavan, K.; Tetrahedron; vol. 42; nb. 16; (1986); p. 4481 - 4492 View in Reaxys I

H 2N

O

O

HO

HO

Rx-ID: 29525761 View in Reaxys 24/361 Yield 92 %

Conditions & References 2.4 General procedure for the amination of aryl halides General procedure: To a solution of aryl halide (1mmol) and ammonium hydroxide (28percent) (1mL, 0.003mmol), 0.005g (0.003mmol) of [(CH3C6H4)3PCH2C6H4CH2OC(O)CH3]2[Pd2Br6] as catalyst was added and the reaction mixture was stirred at 60°C for its appropriate time. The progress of the reaction is followed by TLC. After completion of the reaction, the product was

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extracted with ethyl acetate (3×10mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate (1.5g), filtered and evaporated to give the pure product. The products were characterized by comparison of their spectral (1H NMR and IR) and physical data with those of authentic samples.

With ammonium hydroxide, bis[(2-methylacetatobenzyl)tri(p-tolyl)phosphonium] hexabromodipalladate(II) in neat (no solvent), Time= 5h, T= 60 °C Ghorbani-Choghamarani, Arash; Naghipour, Ali; Heidarizadi, Fateme; Shirkhani, Roghayeh; Notash, Behrouz; Inorganica Chimica Acta; vol. 446; (2016); p. 97 - 102 View in Reaxys 90 %

2.4. General procedure for amination of aryl halides General procedure: To a solution of the aryl halide (1 mmol) and ammonium hydroxide (28percent) (1 mL, 0.003 mmol), 0.005 g (0.003 mmol) of [Ph3PCH2C6H4CH2OC(O)CH3]2[Pd2Br6] as a catalyst were added and the reaction mixture was stirred at 60 °C for an appropriate time. The progress of the reaction was followed by TLC. After completion of the reaction, the product was extracted with ethyl acetate (3 x 10 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate (1.5 g), filtered and evaporated to give the pure product. The products were characterized by a comparison of their spectral (1H NMR and IR) and physical data with those of authentic samples.

With ammonium hydroxide, (2-methylacetatobenzyl)triphenylphosphonium hexabromodipalladate(II), Time= 6h, T= 60 °C Naghipour, Ali; Ghorbani-Choghamarani, Arash; Heidarizadi, Fateme; Notash, Behrouz; Polyhedron; vol. 105; (2016); p.

18 - 26 View in Reaxys

84 %

With ammonium hydroxide, copper(l) iodide, phosphate potassium salt in N,N-dimethyl-formamide, Time= 36h, T= 20 °C , Inert atmosphere Tao, Chuanzhou; Liu, Weiwei; Lv, Aifeng; Sun, Mingming; Tian, Ying; Wang, Qi; Zhao, Jing; Synlett; nb. 9; (2010); p.

1355 - 1358 View in Reaxys

35 %

With copper(l) iodide, ammonium acetate, caesium carbonate in dimethyl sulfoxide, T= 120 °C Irudayanathan, Francis Mariaraj; Noh, Jieun; Choi, Jinseop; Lee, Sunwoo; Advanced Synthesis and Catalysis; vol. 356; nb. 16; (2014); p. 3433 - 3442 View in Reaxys O

H 2N NH

O

HN

HO O

Rx-ID: 30030495 View in Reaxys 25/361 Yield 98 %

Conditions & References 1 :Indigo 2.6 g was dissolved in a mixed solution of sodium hydroxide solution (pH 12) and acetonitrile to obtain an indigo solution. An indigo solution was added as a catalyst together with palladium chloride (17.7 mg) and bromamine-T- (N-bromo-4methylbenzenesulfonamide / sodium) (8.2 g), and the atmosphere was replaced with nitrogen.Indigo was hydrolyzed by stirring for 3 hours while keeping the temperature in the system at 55 ° C. It was carried out while checking whether reaction was appropriate by thin layer chromatogram. From the obtained reaction solution, 2-aminobenzoic acid was separated by a silica gel column using dichloromethane as a developing solvent. 2.5 g (yield: 98percent) of 2-aminobenzoic acid was synthesized.

With bromamine T, sodium hydroxide, palladium dichloride in acetonitrile, Time= 3h, T= 55 °C , pH= 12, Inert atmosphere Patent; THE YOKOHAMA RUBBER COMPANY LIMITED; SAKAI, TOMOYUKI; TANABE, YUSUKE; (7 pag.); JP2016/222575; (2016); (A) Japanese View in Reaxys

96 %

Stage 1: With bromamine B, sodium hydroxide, palladium dichloride in water, acetonitrile, Time= 2.33333h, T= 60 °C , pH= 12 Stage 2: in water, Acidic conditions

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Kumar, C. Vinod; Shivananda; Raju, C. Nagu; Jagadeesh; Synthetic Communications; vol. 40; nb. 23; (2010); p. 3480 3487 View in Reaxys 89 %

With (2,2':6',2''-terpyridine)(pyridine-2-carboxylate)iron(II)chloride, sodium hydroxide in water, acetonitrile, Kinetics, Concentration, Solvent, Temperature, Reagent/catalyst Jagadeesh, Rajenahally V.; Kiran; Bhagat, Pundlik R.; Kumar, S. Senthil; Nithya; Khan, F. Nawaz; Sivakumar; Journal of Molecular Catalysis A: Chemical; vol. 338; nb. 1-2; (2011); p. 92 - 104 View in Reaxys

O

H 2N

O NH

O

NH

O HO

Rx-ID: 43489764 View in Reaxys 26/361 Yield

Conditions & References

85 %

With sulfuric acid, water Kim, Hyunwoo; Park, Gyeongtae; Park, Juhyeon; Chang, Sukbok; ACS Catalysis; vol. 6; nb. 9; (2016); p. 5922 - 5929 View in Reaxys

OH

O

Cl

H 2N

N+ O

Cl – O

Cl –

OH

N+ HO

N Cl OH

Rx-ID: 43603113 View in Reaxys 27/361 Yield

Conditions & References General procedure for regeneration of Sal-(nBu3N+X−) (2a,b) scavengers General procedure: 2 N HCl (3.0 mL) was added to the ionic liquid-supported imines (3a–l) (100 mg) and the mixture was stirred vigorously for 4 h. While the reaction progressed, the color of the imine scavenging products solution was changed to yellowish or colorless. After a completion of the reaction, the reaction mixture was neutralized with NaHCO3 and the isolated scavenger was extracted with DCM (3 × 3.0 mL). The organiclayer was dried with sodium sulfate and evaporated and extracted with a hexane/ethyl acetate mixture (1:1, v/v) to remove amine derivative. After removal of amino component, the residue was dried under reduced pressure to yield the chlorosalicylaldehyde-functionalized ammonium ionic liquids Sal-(nBu3N+X−) (2a,b) in a yield of the range(70–95percent).

With hydrogenchloride in water, Time= 4h Elshaarawy, Reda F.M.; Mokbel, Wafaa A.; El-Sawi, Emtithal A.; Journal of Molecular Liquids; vol. 223; (2016); p. 1123 1132 View in Reaxys

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OH

O

Cl

N+

F P–

F O

H 2N

F

F

O

F

P–

F

OH F

F

N+

F

F

F F HO

N Cl OH

Rx-ID: 43603129 View in Reaxys 28/361 Yield

Conditions & References General procedure for regeneration of Sal-(nBu3N+X−) (2a,b) scavengers General procedure: 2 N HCl (3.0 mL) was added to the ionic liquid-supported imines (3a–l) (100 mg) and the mixture was stirred vigorously for 4 h. While the reaction progressed, the color of the imine scavenging products solution was changed to yellowish or colorless. After a completion of the reaction, the reaction mixture was neutralized with NaHCO3 and the isolated scavenger was extracted with DCM (3 × 3.0 mL). The organiclayer was dried with sodium sulfate and evaporated and extracted with a hexane/ethyl acetate mixture (1:1, v/v) to remove amine derivative. After removal of amino component, the residue was dried under reduced pressure to yield the chlorosalicylaldehyde-functionalized ammonium ionic liquids Sal-(nBu3N+X−) (2a,b) in a yield of the range(70–95percent).

With hydrogenchloride in water, Time= 4h Elshaarawy, Reda F.M.; Mokbel, Wafaa A.; El-Sawi, Emtithal A.; Journal of Molecular Liquids; vol. 223; (2016); p. 1123 1132 View in Reaxys O H 2N

H 2N

O

O N

HO

O

Rx-ID: 43802830 View in Reaxys 29/361 Yield

Conditions & References

42 %

General procedure for reductive cyclization of o-nitrobenzaldehydes to 2,1-benzisoxazoles General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.

With vasicine in ethylene glycol, Time= 48h, T= 80 °C Sharma, Sushila; Kumar, Manoranjan; Bhatt, Vinod; Nayal, Onkar S.; Thakur, Maheshwar S.; Kumar, Neeraj; Singh, Bikram; Sharma, Upendra; Tetrahedron Letters; vol. 57; nb. 45; (2016); p. 5003 - 5008 View in Reaxys O O

O N

H 2N O

O

HO

Rx-ID: 43802831 View in Reaxys 30/361 Yield 58 %

Conditions & References General procedure for reductive cyclization of o-nitrobenzaldehydes to 2,1-benzisoxazoles

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General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.

With vasicine in ethylene glycol, Time= 48h, T= 80 °C Sharma, Sushila; Kumar, Manoranjan; Bhatt, Vinod; Nayal, Onkar S.; Thakur, Maheshwar S.; Kumar, Neeraj; Singh, Bikram; Sharma, Upendra; Tetrahedron Letters; vol. 57; nb. 45; (2016); p. 5003 - 5008 View in Reaxys N

H 2N

H 2N O

H 2N

HO

O

H 2N

O

N

N O

Rx-ID: 43802832 View in Reaxys 31/361 Yield

Conditions & References General procedure for reductive cyclization of o-nitrobenzaldehydes to 2,1-benzisoxazoles General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.

With vasicine in ethylene glycol, Time= 48h, T= 80 °C Sharma, Sushila; Kumar, Manoranjan; Bhatt, Vinod; Nayal, Onkar S.; Thakur, Maheshwar S.; Kumar, Neeraj; Singh, Bikram; Sharma, Upendra; Tetrahedron Letters; vol. 57; nb. 45; (2016); p. 5003 - 5008 View in Reaxys H 2N

H

O

O

HO

Rx-ID: 48260074 View in Reaxys 32/361 Yield

Conditions & References Reaction Steps: 3 1.1: nitric acid; sulfuric acid / 0.67 h / 0 - 15 °C 2.1: potassium permanganate / acetone; water / 1 h 3.1: acetic acid / 0.5 h / 90 °C 3.2: 2 h With potassium permanganate, sulfuric acid, nitric acid, acetic acid in water, acetone Chauhan, Monika; Joshi, Gaurav; Kler, Harveen; Kashyap, Archana; Amrutkar, Suyog M.; Sharma, Praveen; Bhilare, Kiran D.; Chand Banerjee, Uttam; Singh, Sandeep; Kumar, Raj; RSC Advances; vol. 6; nb. 81; (2016); p. 77717 - 77734 View in Reaxys OH

H 2N O O N

HO O

Rx-ID: 308187 View in Reaxys 33/361 Yield 56 %

Conditions & References With potassium tert-butylate in water, Time= 24h, T= 120 °C , Inert atmosphere Zhu, Meijuan; Wang, Chao; Tang, Weijun; Xiao, Jianliang; Tetrahedron Letters; vol. 56; nb. 48; (2015); p. 6758 - 6761 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

With sodium hydroxide Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 664; Bulletin de la Societe Chimique de France; vol. <3> 33; (1905); p. 1165 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8> 6; (1905); p. 412; Annales de Chimie (Cachan, France); vol. <8> 19; (1910); p. 210 View in Reaxys With sodium hydroxide Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 664; Bulletin de la Societe Chimique de France; vol. <3> 33; (1905); p. 1165 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8> 6; (1905); p. 412; Annales de Chimie (Cachan, France); vol. <8> 19; (1910); p. 210 View in Reaxys With sodium hydroxide, ethanol, zinc Freundler; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 882 View in Reaxys Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 371;138,1425; Bulletin de la Societe Chimique de France; vol. <3>31; (1904); p. 880 View in Reaxys

N

O

OH

H 2N O

N

N

NH 2

N HO

Rx-ID: 3775112 View in Reaxys 34/361 Yield 85 %, 92 %

Conditions & References With hydrazine hydrate, aluminium in ethanol, Heating Pasha; Nanjundaswamy; Journal of Chemical Research; nb. 11; (2004); p. 750 - 752 View in Reaxys

88 %, 91 %

With formic acid, zinc in methanol, Time= 0.25h, T= 20 °C Gowda, Shankare; Abiraj; Gowda, D.Channe; Tetrahedron Letters; vol. 43; nb. 7; (2002); p. 1329 - 1331 View in Reaxys

91 %

With ammonium acetate, zinc in methanol, Time= 0.0833333h, T= 20 °C Srinivasa; Abiraj; Gowda, D. Channe; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb.

1; (2004); p. 192 - 195 View in Reaxys

80 %

With zinc, hydrazinium monoformate in methanol, Time= 0.25h, Heating Gowda, Shankare; Abiraj; Gowda, D. Channe; Journal of Chemical Research - Part S; nb. 8; (2002); p. 384 - 385 View in Reaxys

80 %

With ammonium chloride, zinc in methanol, Time= 0.333333h, T= 20 °C Sridhara; Srinivasa; Gowda, D. Channe; Synthetic Communications; vol. 34; nb. 8; (2004); p. 1441 - 1446 View in Reaxys With potassium phosphate buffer, Clostridium diaphorase, NAD, Time= 0.0833333h, T= 25 °C , inhibitor constant; var. inhibitors

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yatome, Chizuko; Fujimi, Kazuhiko; Ogawa, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 65; nb. 9; (1992); p.

2349 - 2351 View in Reaxys With ammonium formate, magnesium in methanol, Time= 0.333333h, T= 20 °C Abiraj; Gowda, Shankare; Gowda, D. Channe; Journal of Chemical Research - Part S; nb. 5; (2003); p. 299 - 300 View in Reaxys With ammonium bromide, aluminium in methanol, Time= 0.166667h, sonication Pasha; Jayashankara; Journal of Chemical Research; nb. 4; (2004); p. 282 - 283 View in Reaxys With hydrogen in ethanol, Time= 0.0333333h, T= 20 °C , aq. buffer Dai, Yunqian; Lim, Byungkwon; Yang, Yong; Cobley, Claire M.; Li, Weiyang; Cho, Eun Chul; Grayson, Benjamin; Fanson, Paul T.; Campbell, Charles T.; Sun, Yueming; Xia, Younan; Angewandte Chemie - International Edition; vol. 49; nb. 44; (2010); p. 8165 - 8168 View in Reaxys With metallothionein δ-domain tetranuclear iron(II) complex, Time= 6h, T= 25 °C , pH= 8, Inert atmosphere, aq. phosphate buffer Sano, Yohei; Onoda, Akira; Sakurai, Rie; Kitagishi, Hiroaki; Hayashi, Takashi; Journal of Inorganic Biochemistry; vol.

105; nb. 5; (2011); p. 702 - 708 View in Reaxys With sodium tetrahydroborate, water, C60 fullerene, sodium hydroxide, Time= 5h, T= 20 °C , pH= 11, UV-irradiation Guo, Yong; Li, Wengang; Yan, Jingjing; Moosa, Basem; Amad, Ma'An; Werth, Charles J.; Khashab, Niveen M.; Chemistry - An Asian Journal; vol. 7; nb. 12; (2012); p. 2842 - 2847 View in Reaxys With 1,4-dihydronicotinamide adenine dinucleotide, recombinant Escherichia coli CpXFMN flavin mononucleotide-containing azobenzene reductase in aq. buffer, T= 30 °C , pH= 7.4, Enzymatic reaction, Kinetics, pH-value, Reagent/catalyst, Temperature Langer, Simone; Nakanishi, Shinobu; Mathes, Tilo; Knaus, Tanja; Binter, Alexandra; Macheroux, Peter; Mase, Tomoko; Miyakawa, Takuya; Tanokura, Masaru; Mack, Matthias; Biochemistry; vol. 52; nb. 25; (2013); p. 4288 - 4295 View in Reaxys With FMN-dependent NADH-azoreductase from Burkholderia thailandensis, NADH, Reagent/catalyst Kolb, Roman; Bach, Nina C.; Sieber, Stephan A.; Chemical Communications; vol. 50; nb. 4; (2014); p. 427 - 429 View in Reaxys With sodium tetrahydroborate, sodium hydroxide in water, Time= 0.75h, T= 20 °C , UV-irradiation Mazzier, Daniela; Carraro, Francesco; Crisma, Marco; Rancan, Marzio; Toniolo, Claudio; Moretto, Alessandro; Soft Matter; vol. 12; nb. 1; (2015); p. 238 - 245 View in Reaxys H 2N

H 2N

O N

HO

Rx-ID: 4380465 View in Reaxys 35/361 Yield 62 %

Conditions & References With phosphate buffer, Time= 24h, T= 30 °C , rhodococcus rhodocrous AJ270, pH 7.0 Meth-Cohn, Otto; Wang, Mei-Xiang; Tetrahedron Letters; vol. 36; nb. 52; (1995); p. 9561 - 9564 View in Reaxys

62.3 %

With potassium phosphate buffer, Time= 24h, T= 30 °C , Rhodococcus sp. AJ270 cells

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Meth-Cohn, Otto; Wang, Mei-Xiang; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1997); p. 1099 - 1104 View in Reaxys With pro-nitro010, water, Enzymatic reaction, Reagent/catalyst Black, Gary W.; Brown, Nicola L.; Perry, Justin J. B.; Randall, P. David; Turnbull, Graeme; Zhang, Meng; Chemical Communications; vol. 51; nb. 13; (2015); p. 2660 - 2662 View in Reaxys With nitrilase from Gordonia terrae in aq. phosphate buffer, Time= 1h, T= 35 °C , pH= 8, Enzymatic reaction Kumar, Vijay; Seth, Amit; Kumari, Vijaya; Kumar, Virender; Bhalla, Tek C.; Protein and Peptide Letters; vol. 22; nb. 1; (2015); p. 52 - 62 View in Reaxys

NH 2

H

O

NH 2

H 2N

H O

HO

HO NH 2 O

O

HO

Rx-ID: 4873646 View in Reaxys 36/361 Yield

Conditions & References With potassium phosphate buffer, kynureninase, pyridoxal 5'-phosphate in water, T= 25 °C , Km value, Vmax value, other reactant: 2S-<2-(2)H>-kynurenine, deuterium kinetic isotope effect, other solvent: D2O, pH 7.0, Mechanism, Kinetics Ross, Fiona C.; Botting, Nigel P.; Leeson, Paul D.; Tetrahedron; vol. 53; nb. 46; (1997); p. 15761 - 15770 View in Reaxys With bacterial kynureninase from Pseudomonas fluorescens in various solvent(s), T= 37 °C , pH= 7.5, Enzyme kinetics Fitzgerald, Deirdre H.; Muirhead, Karen M.; Botting, Nigel P.; Bioorganic and Medicinal Chemistry; vol. 9; nb. 4; (2001); p.

983 - 989 View in Reaxys With homo sapiens kynureninase, pyridoxal 5'-phosphate, T= 37 °C , pH= 8.0, aq. phosphate buffer, Enzymatic reaction, Kinetics, Reagent/catalyst Lima, Santiago; Kumar, Sunil; Gawandi, Vijay; Momany, Cory; Phillips, Robert S.; Journal of Medicinal Chemistry; vol.

52; nb. 2; (2009); p. 389 - 396 View in Reaxys With pyridoxal 5'-phosphate, Pseudomonas fluorescens L-kynurenine hydrolase Y226F mutant in aq. phosphate buffer, T= 37 °C , pH= 8, Enzymatic reaction, Kinetics, pH-value Phillips, Robert S.; Scott, Israel; Paulose, Riya; Patel, Akshay; Barron, Taylor Colt; FEBS Journal; vol. 281; nb. 4; (2014); p. 1100 - 1109 View in Reaxys Br

H 2N

O

O

HO

HO

Rx-ID: 29517848 View in Reaxys 37/361 Yield 91 %

Conditions & References Stage 1: With copper(l) iodide, sodium azide, ethanol, caesium carbonate, T= 20 - 95 °C , Inert atmosphere, Sealed tube Stage 2: With hydrogenchloride in water, pH= 2 - 3 Zhao, Haibo; Fu, Hua; Qiao, Renzhong; Journal of Organic Chemistry; vol. 75; nb. 10; (2010); p. 3311 - 3316 View in Reaxys

87 %

With diethylenetriaminopentaacetic acid, ammonia, copper(II) oxide, potassium hydroxide in water, Time= 12h, T= 100 °C

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yang, Bo; Liao, Lihao; Zeng, Yongheng; Zhu, Xinhai; Wan, Yiqian; Catalysis Communications; vol. 45; (2014); p. 100 103 View in Reaxys

O

N

H 2N O H N

O

HN

O

O

OH HO

O

N N

Rx-ID: 38917567 View in Reaxys 38/361 Yield

Conditions & References With hydrogenchloride in water, Time= 14h, T= 105 °C Peng, Jixing; Gao, Huquan; Zhang, Xiaomin; Wang, Shuai; Wu, Chongming; Gu, Qianqun; Guo, Peng; Zhu, Tianjiao; Li, Dehai; Journal of Natural Products; vol. 77; nb. 10; (2014); p. 2218 - 2223 View in Reaxys

O

N

H 2N O H N

O

HN

O HO

O

OH HO

O

N N

Rx-ID: 38917568 View in Reaxys 39/361 Yield

Conditions & References With hydrogenchloride in water, Time= 14h, T= 105 °C Peng, Jixing; Gao, Huquan; Zhang, Xiaomin; Wang, Shuai; Wu, Chongming; Gu, Qianqun; Guo, Peng; Zhu, Tianjiao; Li, Dehai; Journal of Natural Products; vol. 77; nb. 10; (2014); p. 2218 - 2223 View in Reaxys

O

N

H 2N O

HO

H N

O

HN

O HO

O

OH HO

O

N N

Rx-ID: 38917569 View in Reaxys 40/361 Yield

Conditions & References With hydrogenchloride in water, Time= 14h, T= 105 °C Peng, Jixing; Gao, Huquan; Zhang, Xiaomin; Wang, Shuai; Wu, Chongming; Gu, Qianqun; Guo, Peng; Zhu, Tianjiao; Li, Dehai; Journal of Natural Products; vol. 77; nb. 10; (2014); p. 2218 - 2223 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O N N H

H

O HN O

O

HN

O

HO

HO N H

NH 2 NH

H 2N

H

O

O

O

HO

N

O

Rx-ID: 38917570 View in Reaxys 41/361 Yield

Conditions & References With hydrogenchloride in water, Time= 14h, T= 105 °C Peng, Jixing; Gao, Huquan; Zhang, Xiaomin; Wang, Shuai; Wu, Chongming; Gu, Qianqun; Guo, Peng; Zhu, Tianjiao; Li, Dehai; Journal of Natural Products; vol. 77; nb. 10; (2014); p. 2218 - 2223 View in Reaxys H 2N H 2N O O

O N

O HO

O

Rx-ID: 38921434 View in Reaxys 42/361 Yield

Conditions & References 2.2. Kinetic procedure Kinetic measurements were performed using a Shimadzu UV–Visspectrophotometer (Model UV-2550) equipped with a thermostatedcell holder whose temperature was controlled within 25 ± 0.1 °C, in a1.0 cm quartz cuvette. Reaction solutions were prepared by combiningthe appropriate amounts of water and acetonitrile, the borate buffer ofpH = 9.18 (the final concentration of 5.0 mmol dm−3) and salts andthen were left to stand for about 30 min in a Taitec constant temperaturewaterbath at 50±0.1 °C in order to reach the thermal equilibrium.Prior to the beginning of the reaction, a stock solution of the substrate(p-NPA) (5.0 × 10−3 mol dm−3) in MeCN was prepared since the substrateis sparingly soluble in pure water. Reactions were initiated bytransferring 1.0 mL of the stock solution into a reaction vessel (50 mL)to reach the final substrate concentration of 1.0 × 10−4 mol dm−3.The samplings of 3–4mLwere carried out fromreaction solutions at certaintime intervals and the sampled solutions were immediately dippedinto an icewater bath. The reaction progress was then followed spectrophotometricallyby monitoring the liberation of p-nitrophenoxide ion atδmax = ca. 400 nm as a function of time. The apparent first order rateconstants were obtained from the slopes of plot of ln (Aδ − At) vs. t,where Aδ and At are the absorbance values at the reaction final and attime t, respectively. All rate constants were obtained from linear plotswith correlation coefficients (R2) of normally 0.999 or more.

With sodium azide, water in acetonitrile, T= 50 °C , pH= 9.18, Kinetics, pH-value, Reagent/catalyst, Temperature Bayissa, Leta Danno; Ohmae, Yoshihito; Hojo, Masashi; Journal of Molecular Liquids; vol. 199; (2014); p. 294 - 300 View in Reaxys H 2N O

O N O

HO

Rx-ID: 280984 View in Reaxys 43/361 Yield

Conditions & References With potassium hydroxide, T= 200 °C Lock; Chemische Berichte; vol. 73; (1940); p. 1377,1381 View in Reaxys With water, Einw. eines Gluehkoerpers Loeb; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 8; (1902); p. 775

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys With sodium hydroxide Preuss; Binz; ; vol. 13; (1900); p. 385 View in Reaxys Patent; Bad. Anilin- u. Sodaf.; DE114839 View in Reaxys With sodium hydroxide, T= 150 °C , unter Druck Preuss; Binz; ; vol. 13; (1900); p. 385 View in Reaxys Patent; Bad. Anilin- u. Sodaf.; DE114839 View in Reaxys Reaction Steps: 2 1: potassium permanganate; tetrabutylammomium bromide 2: hydrogen; 10% palladium on activated charcoal With potassium permanganate, 10% palladium on activated charcoal, tetrabutylammomium bromide, hydrogen Dong, Kui-Kui; Zhou, Hua-Hong; Guo, A-Rong; Chen, Tian; Wang, Yu-Liang; Asian Journal of Chemistry; vol. 25; nb. 2; (2013); p. 1039 - 1042 View in Reaxys Reaction Steps: 2 1: potassium permanganate; water / 8 h / Reflux 2: 10% palladium on activated carbon; Degussa type / tetrahydrofuran / 24 h / 20 °C With potassium permanganate, 10% palladium on activated carbon; Degussa type, water in tetrahydrofuran Yu, Yongguo; Wu, Jianbo; Lei, Fan; Chen, Lei; Wan, Weili; Hai, Li; Guan, Mei; Wu, Yong; Letters in Drug Design and Discovery; vol. 10; nb. 4; (2013); p. 369 - 373 View in Reaxys Br

H 2N

O

O

HO

HO

H 2N

H 2N

Rx-ID: 34978692 View in Reaxys 44/361 Yield

Conditions & References

71 %, 21 %

2.2 General procedure for amination General procedure: A mixture of substrate (0.25 mmol), complex 1 (2.5 × 10− 3 mmol), Cs2CO3 (1 mmol), Conc. NH3(aq) (0.5 mL) and TBAB (0.25 mmol) in water (0.5 mL) were loaded in a sealed reaction tube. The reaction temperature was increased to 110–140 °C and the reaction mixture was stirred for 8–24 h. After cooling to RT, the reaction mixture was poured into a saturated NaCl solution, extracted with ethyl acetate and dried over anhydrous MgSO4. After removal of solvents, the residue was re-crystallized or chromatographed on silica gel. All products were characterized by NMR spectroscopy and were consistent with the literature data.

With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3], tetrabutylammomium bromide, ammonia, caesium carbonate in water, Time= 16h, T= 110 - 120 °C , Sealed tube Liao, Bei-Sih; Liu, Shiuh-Tzung; Catalysis Communications; vol. 32; (2013); p. 28 - 31 View in Reaxys

O

H N

OH

N

H N

O OH

O

O

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O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

H 2N O O

C

N H

O

HO

O HO

O OH

Rx-ID: 35750356 View in Reaxys 45/361 Yield

Conditions & References

86 %

2 : 4.2. The bulk oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinoline (PhquinH2) 4.2 The bulk oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinoline (PhquinH2) PhquinH2 (237.25 mg, 1 mmol) in a DMSO/H2O mixture (10 mL), at 25 °C, 1 bar O2 pressure were oxygenated for 6 h in a thermostated reaction vessel attached to a buret.

The evolved CO was determined by GC-MS from the gas phase and was found to be 0.86 mmol (86percent).

The reaction mixture was acidified and treated with diazomethane and then analyzed by GC. Gas chromatogram and the conditions with the results are shown in SFig. 11 .

With oxygen in water, dimethyl sulfoxide, Time= 6h, T= 25 °C , p= 750.075Torr , Schlenk technique, Kinetics, Mechanism, Concentration, pH-value, Temperature Czaun, Miklos; Speier, Gabor; Kaizer, Jozsef; El Bakkali-Taheri, Nadia; Farkas, Etelka; Tetrahedron; vol. 69; nb. 32; (2013); p. 6666 - 6672 View in Reaxys

Br Br

O

H N

OH

H N

O

OH O

Br

Br O

O

H 2N

N

O

Br

NH

HO

O

O

HO

OH

O O

Rx-ID: 35750357 View in Reaxys 46/361 Yield

Conditions & References With oxygen in water, dimethyl sulfoxide, Time= 6h, T= 20 °C , pH= 10.4, Schlenk technique Czaun, Miklos; Speier, Gabor; Kaizer, Jozsef; El Bakkali-Taheri, Nadia; Farkas, Etelka; Tetrahedron; vol. 69; nb. 32; (2013); p. 6666 - 6672 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

O

O O

H N

N NH

O

O

OH O

O

OH O

H 2N

O

O O

O

N H

HO HO

O

O

OH

Rx-ID: 35750359 View in Reaxys 47/361 Yield

Conditions & References With oxygen in water, dimethyl sulfoxide, Time= 6h, T= 20 °C , pH= 10.4, Schlenk technique Czaun, Miklos; Speier, Gabor; Kaizer, Jozsef; El Bakkali-Taheri, Nadia; Farkas, Etelka; Tetrahedron; vol. 69; nb. 32; (2013); p. 6666 - 6672 View in Reaxys O

O

O

N

N

O H N

O

HN

O OH

OH O

O O

N O

N

H 2N

O

O

O

O

O

N

N

NH O

O

O

OH

OH

HO

O

O

Rx-ID: 35750361 View in Reaxys 48/361 Yield

Conditions & References With oxygen in water, dimethyl sulfoxide, Time= 6h, T= 20 °C , pH= 10.4, Schlenk technique Czaun, Miklos; Speier, Gabor; Kaizer, Jozsef; El Bakkali-Taheri, Nadia; Farkas, Etelka; Tetrahedron; vol. 69; nb. 32; (2013); p. 6666 - 6672 View in Reaxys H 2N O

HO

Rx-ID: 36205542 View in Reaxys 49/361 Yield

Conditions & References Reaction Steps: 3

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

1: nitric acid; sulfuric acid / 2 h / 70 °C 2: potassium permanganate; water / 8 h / Reflux 3: 10% palladium on activated carbon; Degussa type / tetrahydrofuran / 24 h / 20 °C With potassium permanganate, sulfuric acid, 10% palladium on activated carbon; Degussa type, water, nitric acid in tetrahydrofuran Yu, Yongguo; Wu, Jianbo; Lei, Fan; Chen, Lei; Wan, Weili; Hai, Li; Guan, Mei; Wu, Yong; Letters in Drug Design and Discovery; vol. 10; nb. 4; (2013); p. 369 - 373 View in Reaxys

O

HN Cl

NH

S O

O

NH S O

O

Cl

N

O

N

HN

Cl

HO

O

O

O S

O

S O

O

H 2N

H N

S

S

NH 2

NH 2

Rx-ID: 36433022 View in Reaxys 50/361 Yield 44.9 %, 3.6 %, 36.1 %

Conditions & References With water, sodium hydroxide, Time= 42h, T= 20 °C , Reflux Brzozowski, Zdzislaw; Slawinski, Jaroslaw; Journal of Heterocyclic Chemistry; vol. 50; nb. 5; (2013); p. 1099 - 1107 View in Reaxys

O

O

H 2N

O

HN Cl

O

N

S

HO

O

O

NH

S O

NH

S

OH

O NH

O

HN Cl

HN

O

S O

O

O

Rx-ID: 36433035 View in Reaxys 51/361 Yield 94 %, 73 %

Conditions & References Stage 1: With water, sodium hydroxide, Time= 8h, T= 20 °C Stage 2: With hydrogenchloride, water, pH= 3 Brzozowski, Zdzislaw; Slawinski, Jaroslaw; Journal of Heterocyclic Chemistry; vol. 50; nb. 5; (2013); p. 1099 - 1107 View in Reaxys H 2N

H 2N

O

H 2N

HO

HO

Rx-ID: 34456923 View in Reaxys 52/361 Yield

Conditions & References With N-hydroxyphthalimide, oxygen, cobalt(II) acetate, T= 80 °C , p= 760.051Torr , Ionic liquid

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Lu, Tingting; Lu, Ming; Yu, Wang; Liu, Zhongjie; Croatica Chemica Acta; vol. 85; nb. 3; (2012); p. 277 - 282 View in Reaxys H 2N NH

O

HO

Rx-ID: 30030483 View in Reaxys 53/361 Yield

Conditions & References

95 %

Stage 1: With bromamine B, sodium hydroxide, palladium dichloride in water, acetonitrile, Time= 3.5h, T= 60 °C , pH= 12 Stage 2: in water, Acidic conditions Kumar, C. Vinod; Shivananda; Raju, C. Nagu; Jagadeesh; Synthetic Communications; vol. 40; nb. 23; (2010); p. 3480 3487 View in Reaxys

95 %

With ruthenium trichloride, osmium(VIII) oxide, bromamine B, sodium hydroxide in water, acetonitrile, Time= 5h, T= 39.84 °C Karthikeyan; Jagadeesh, Rajenahally V.; Sree Sandhya; Puttaswamy; Nithya; Kumar, S. Senthil; Bhagat; Applied Organometallic Chemistry; vol. 25; nb. 1; (2011); p. 34 - 46 View in Reaxys With ruthenium trichloride, sodium hydroxide in water, acetonitrile, T= 39.84 °C , Kinetics, Mechanism, Concentration, Reagent/catalyst, Temperature, Solvent Karthikeyan; Jagadeesh, Rajenahally V.; Sree Sandhya; Puttaswamy; Nithya; Kumar, S. Senthil; Bhagat; Applied Organometallic Chemistry; vol. 25; nb. 1; (2011); p. 34 - 46 View in Reaxys

N

O

OH

NH 2

HO N

N

N

H 2N

N

O

HO

OH N

Rx-ID: 30957066 View in Reaxys 54/361 Yield

Conditions & References in toluene, T= 28 °C , Kinetics Sen Gupta, Susanta K.; Mishra, Sangeeta; Journal of Physical Chemistry A; vol. 115; nb. 18; (2011); p. 4616 - 4623 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

NH 2

H 2N O

O

HO

Rx-ID: 32581399 View in Reaxys 55/361 Yield

Conditions & References With alpha cyclodextrin in water, Alkaline conditions, Kinetics, Reagent/catalyst Iglesias, Emilia; Photochemical and Photobiological Sciences; vol. 10; nb. 4; (2011); p. 531 - 542 View in Reaxys Cl

H 2N

O

O

HO

HO

Rx-ID: 827725 View in Reaxys 56/361 Yield 94 %

Conditions & References With ammonium hydroxide, caesium carbonate in 1-methyl-pyrrolidin-2-one, Time= 24h, T= 80 °C Xu, Hanhui; Wolf, Christian; Chemical Communications; nb. 21; (2009); p. 3035 - 3037 View in Reaxys

90 %

Stage 1: With copper(l) iodide, sodium azide, ethanol, caesium carbonate, N,N`-dimethylethylenediamine, T= 20 - 95 °C , Inert atmosphere, Sealed tube Stage 2: With hydrogenchloride in water, pH= 2 - 3 Zhao, Haibo; Fu, Hua; Qiao, Renzhong; Journal of Organic Chemistry; vol. 75; nb. 10; (2010); p. 3311 - 3316 View in Reaxys With ammonia, chromium Chakrabarty; Dutt; Journal of the Indian Chemical Society; vol. 5; (1928); p. 514; Chem. Zentralbl.; vol. 100; nb. I; (1929); p.

501 View in Reaxys With ammonium hydroxide, copper, T= 125 °C , unter Druck Patent; Hoechster Farbw.; DE145604 View in Reaxys With ammonia, potassium carbonate, copper(I) bromide in N,N-dimethyl-formamide, Time= 1h, T= 150 °C Smith, Adrian L.; Thomson, Christopher G.; Leeson, Paul D.; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 13; (1996); p. 1483 - 1486 View in Reaxys

HO

O

OH H 2N

N N

O

HO

NH 2

HO

Rx-ID: 1975823 View in Reaxys 57/361 Yield

Conditions & References With sodium hydrogensulfite in ethanol, water, T= 25 °C , activation energy, Rate constant, Kinetics, Thermodynamic data Mahmoud, M. R.; Gabr, R. M.; Hamed, M. M. A.; Bulletin de la Societe Chimique de France; vol. 1; nb. 9-10; (1983); p. 215 - 219 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

With sodium dithionite, water in dimethyl sulfoxide, T= 20 °C , pH= 7.4, phosphate buffer, Kinetics, Concentration Leriche, Geoffray; Budin, Ghyslain; Brino, Laurent; Wagner, Alain; European Journal of Organic Chemistry; nb. 23; (2010); p. 4360 - 4364 View in Reaxys O H 2N

OH

H 2N

O O

N N

O

OH HO

OH

Rx-ID: 29683042 View in Reaxys 58/361 Yield

Conditions & References With sodium dithionite, water in dimethyl sulfoxide, Time= 0.00138889h, T= 20 °C , pH= 7.4, phosphate buffer, Kinetics, Concentration Leriche, Geoffray; Budin, Ghyslain; Brino, Laurent; Wagner, Alain; European Journal of Organic Chemistry; nb. 23; (2010); p. 4360 - 4364 View in Reaxys

HO H 2N

O

O

O

HO

OH

HO

O

Rx-ID: 30707239 View in Reaxys 59/361 Yield

Conditions & References With Sulfolobus solfataricus anthranilate synthase TrpE/TrpG, Enzymatic reaction Sridharan, Sudharsan; Howard, Nigel; Kerbarh, Olivier; Blaszczyk, Michal; Abell, Chris; Blundell, Tom L.; Journal of Molecular Biology; vol. 397; nb. 1; (2010); p. 290 - 300 View in Reaxys H 2N H 2N

O O

O HO

Rx-ID: 31232779 View in Reaxys 60/361 Yield

Conditions & References With sodium perchlorate, water, sodium hydroxide, T= 25 °C , Kinetics Nummert, Vilve; Piirsalu, Mare; Koppel, Ilmar A.; Journal of Physical Organic Chemistry; vol. 23; nb. 6; (2010); p. 497 504 View in Reaxys H 2N H 2N

O O

HO

O HO

Rx-ID: 8752371 View in Reaxys 61/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With sodium hydroxide in dimethyl sulfoxide, T= 25 °C , Kinetics, Further Variations: reagent concentrations Bauerova, Ingrid; Ludwig, Miroslav; Collection of Czechoslovak Chemical Communications; vol. 66; nb. 5; (2001); p. 770 784 View in Reaxys With water, T= 50 °C , pH= 2 - 11, Kinetics Fife, Thomas H.; Singh, Randhir; Bembi, Ramesh; Journal of Organic Chemistry; vol. 67; nb. 10; (2002); p. 3179 - 3183 View in Reaxys With tetrabutylammomium bromide, tetra(n-butyl)ammonium hydroxide, water, T= 25 °C , Kinetics Nummert, Vilve; Piirsalu, Mare; Vahur, Signe; Travnikova, Oksana; Koppel, Ilmar A.; Collection of Czechoslovak Chemical Communications; vol. 74; nb. 1; (2009); p. 29 - 42 View in Reaxys O

OH

HO OH

O H+

N

O

N H

H 2N

OH

Rx-ID: 28215732 View in Reaxys 62/361 Yield

Conditions & References With copper(II) ion in water, Acidic conditions Wang, Qiang-Li; Zhang, Han; Jiang, Yun-Bao; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 29 - 31 View in Reaxys

O

O

H 2N O

H N

N

HO

O

Rx-ID: 28522836 View in Reaxys 63/361 Yield

Conditions & References

90 %

Stage 1: With sodium hydroxide, water, Time= 18h, Reflux Stage 2: With hydrogenchloride in water, pH= 2 Houlden, Chris E.; Hutchby, Marc; Bailey, Chris D.; Ford, J.Gair; Tyler, Simon N. G.; Gagne, Michel R.; Lloyd-Jones, Guy C.; Booker-Milburn, Kevin I.; Angewandte Chemie - International Edition; vol. 48; nb. 10; (2009); p. 1830 - 1833 View in Reaxys

90 %

Stage 1: With sodium hydroxide, Time= 18h, Reflux Stage 2: With hydrogenchloride in water, pH= 2 Hutchby, Marc; Houlden, Chris E.; Gair Ford; Tyler, Simon N. G.; Gagne, Michel R.; Lloyd-Jones, Guy C.; BookerMilburn, Kevin I.; Angewandte Chemie - International Edition; vol. 48; nb. 46; (2009); p. 8721 - 8724 View in Reaxys O H 2N

N

N

N

OH O

HO

Rx-ID: 4880352 View in Reaxys 64/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield 98 %

Conditions & References With chloro-trimethyl-silane, sodium iodide in acetonitrile, Time= 0.166667h, Ambient temperature Kamal, Ahmed; Rao, N. Venugopal; Laxman; Tetrahedron Letters; vol. 38; nb. 39; (1997); p. 6945 - 6948 View in Reaxys

98 %

With chloro-trimethyl-silane, sodium iodide in acetonitrile, Time= 0.166667h, Ambient temperature, alkyl, aryl, aroyl, variously substituted azides, chemoselective transformation into amines, Product distribution Kamal, Ahmed; Rao, N. Venugopal; Laxman; Tetrahedron Letters; vol. 38; nb. 39; (1997); p. 6945 - 6948 View in Reaxys

98 %

With hydrogen, MCM-silylamine Pd(II) in methanol, Time= 3h, T= 20 °C , Reduction Kantam, M. Lakshmi; Chowdari, N. Srcenivasa; Rahman, Ateeq; Choudary; Synlett; nb. 9; (1999); p. 1413 - 1414 View in Reaxys

98 %

With hydrogen, dopamine terminated NiFe2O4, palladium in ethanol, Time= 0.25h, p= 760.051Torr Guin, Debanjan; Baruwati, Babita; Manorama, Sunkara V.; Organic Letters; vol. 9; nb. 7; (2007); p. 1419 - 1421 View in Reaxys

96 %

With ammonium chloride, indium in ethanol, Time= 1h, Heating, Reduction Reddy, G. Vidyasagar; Rao, G. Venkat; Iyengar; Tetrahedron Letters; vol. 40; nb. 20; (1999); p. 3937 - 3938 View in Reaxys

96 %

With ammonia, iron(II) sulfate in methanol, water, Time= 2.5h, T= 20 °C , Reduction Kamal; Laxman; Arifuddin; Tetrahedron Letters; vol. 41; nb. 40; (2000); p. 7743 - 7746 View in Reaxys

96 %

With hexacarbonyl molybdenum in ethanol, Time= 6.5h, Heating Iyer, Suresh; Kulkarni, Girish M.; Synthetic Communications; vol. 34; nb. 4; (2004); p. 721 - 725 View in Reaxys

95 %

With hydrogen iodide, Time= 1.5h, T= 20 °C Kamal, Ahmed; Reddy; Reddy, D.Rajasekhar; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6629 - 6631 View in Reaxys

90 %

With iron(III) chloride, N,N-Dimethylhydrazine in methanol, Time= 1h, Ambient temperature Kamal, Ahmed; Reddy, B. S. Narayan; Chemistry Letters; nb. 7; (1998); p. 593 - 594 View in Reaxys

90 %

With sodium tetrahydroborate, zirconium(IV) chloride in tetrahydrofuran, Time= 0.333333h, T= 0 - 35 °C , Reduction Purushothama Chary; Raja Ram; Salahuddin; Iyengar; Synthetic Communications; vol. 30; nb. 19; (2000); p. 3559 - 3563 View in Reaxys

85 %

With Saccharomyces cerevisiae in ethanol, Time= 6h, phosphate buffer (pH 7.2) Kamal, Ahmed; Damayanthi; Reddy, B. S. Narayan; Lakminarayana; Reddy, B. S. Praveen; Chemical Communications; nb. 11; (1997); p. 1015 - 1016 View in Reaxys

85 %

With ammonium formate, zinc in methanol, Time= 0.166667h, T= 20 °C Srinivasa; Nalina; Abiraj; Gowda, D. Channe; Journal of Chemical Research - Part S; nb. 10; (2003); p. 630 - 631 View in Reaxys

85 %

With ammonium formate, zinc in methanol, Time= 0.333333h, T= 20 °C Kamal, Ahmed; Srinivasa Reddy; Rajendra Prasad; Hari Babu; Ramana, A. Venkata; Tetrahedron Letters; vol. 45; nb. 34; (2004); p. 6517 - 6521 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

85 %

With boron trifluoride diethyl etherate, sodium iodide in acetonitrile, Time= 0.5h, T= 20 °C Kamal, Ahmed; Shankaraiah; Markandeya; Reddy, Ch. Sanjeeva; Synlett; nb. 9; (2008); p. 1297 - 1300 View in Reaxys

80 %

With iron(III) chloride, zinc in ethanol, Time= 6h, T= 20 °C , Reduction Pathak, Diganta; Laskar, Dhrubojyoti D.; Prajapati, Dipak; Sandhu, Jagir S.; Chemistry Letters; nb. 7; (2000); p. 816 - 817 View in Reaxys

75 %

With dicobalt octacarbonyl in water, Time= 5h, T= 20 °C Yadav; Reddy; Satheesh; Raghavender Rao; Chemistry Letters; vol. 34; nb. 3; (2005); p. 340 - 341 View in Reaxys O N

H 2N

O O

F

O

F HO

OH

F

Rx-ID: 28026660 View in Reaxys 65/361 Yield

Conditions & References

97 %

7 :The 2-aminobenzoic acid used as a starting material in this example could be prepared in one step from the corresponding 2nitrobenzoic acid: 2-amino-4-trifluoromethylbenzoic acid10percent palladium on active charcoal (1.00 g) was added to a solution of 2-nitro-4-trifluoromethylbenzoic acid (10.0 g, 42.6 mmol) in methanol (20 ml) and hydrogenation was carried out at room temperature under a hydrogen atmosphere of 3 bar until 128 mmol of hydrogen had been taken up. The mixture was filtered over silica gel and the filtrate was concentrated in vacuo.Yield: 8.48 g (97percent), white solid.Melting point: 174-178° C. With sodium hydroxide, 10% palladium on activated carbon; Degussa type in methanol, T= 20 °C , p= 9750.98Torr Patent; Gruenenthal GmbH; US2008/293749; (2008); (A1) English View in Reaxys H N

O

O

O N H

O

N

H N

H 2N

O

O

N

O

N HO

O

O

Rx-ID: 10281102 View in Reaxys 66/361 Yield

Conditions & References

29 %

With triethylamine in tetrahydrofuran, Time= 8h, T= 80 °C Duvall, Jeremy R.; Wu, Fanghui; Snider, Barry B.; Journal of Organic Chemistry; vol. 71; nb. 22; (2006); p. 8579 - 8590 View in Reaxys H 2N

H 2N O

O

O

I

HO

Rx-ID: 9648148 View in Reaxys 67/361 Yield 62 %

Conditions & References in acetonitrile, T= 5 °C , Electrolysis, atmospheric pressure, Product distribution, Further Variations: Temperatures, current density

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Korbi, B. Haouas; Adhoum; Boujlel; Synthetic Communications; vol. 34; nb. 14; (2004); p. 2557 - 2564 View in Reaxys

O

O

O NH

O

NH 2

H 2N O

O

O HO

Rx-ID: 9691057 View in Reaxys 68/361 Yield

Conditions & References

85 %, 10 %

With H-δ zeolite in dichloromethane, Time= 10h, Heating Tillu, Vasudha H.; Wakharkar, Radhika D.; Pandey, Rajesh K.; Kumar, Pradeep; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 5; (2004); p. 1004 - 1007 View in Reaxys H 2N

O

HO

Rx-ID: 5820547 View in Reaxys 69/361 Yield 98.0%

Conditions & References VI : EXAMPLE VI EXAMPLE VI A 20 g quantity of piperidinium N-(3,4-dimethoxycinnamoyl)anthranilate is dissolved in 60 ml of water with heating, and the resultant aqueous solution is added dropwise to 45 ml of diluted hydrochloric acid (5 ml of conc. hydrochloric acid and 40 ml of water) with stirring.

The precipitated crystals which form are collected by filtration, washed with water and then dried at 90°-100° C. under reduced pressure for 3 hours to yield 15.5 g of N-(3,4-dimethoxycinnamoyl)anthranilic acid (98.0percent yield), m.p. 208°-208.5° C. The compound structure is confirmed by elemental analysis, and by IR and NMR spectroscopy.

Patent; Kissei Pharmaceutical Co., Ltd.; US4486597; (1984); (A) English View in Reaxys

98%

VII : EXAMPLE VII EXAMPLE VII A 20 g quantity of morpholinium N-(3,4-dimethoxycinnamoyl)anthranilate is dissolved in 40 ml of water and the resultant solution is added dropwise to 45 ml of diluted hydrochloric acid (5 ml of conc. hydrochloric acid and 40 ml of water) with stirring.

The precipitated crystals which form are collected by filtration, washed with water and then dried at 90°-100° C. under reduced pressure for 3 hours to yield 15.5 g of N-(3,4-dimethoxycinnamoyl)anthranilic acid (98percent yield).

The compound is confirmed as identical to that obtained in EXAMPLE VI. Patent; Kissei Pharmaceutical Co., Ltd.; US4486597; (1984); (A) English View in Reaxys Herstellung von <δ-14 C>Anthranilsaeure Murray; Ronzio; ; (1958); p. 316 View in Reaxys Kurono; Ikeda; Uekama; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 340 - 345 View in Reaxys Crabtree,E.V. et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 268 - 272 View in Reaxys Bain,D.I.; Smalley,R.K.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 1593 - 1597 View in Reaxys ERGE; GROEGER; MOTHES; Archiv der Pharmazie; vol. 295 /67; (1962); p. 474 - 475 View in Reaxys Bouchet et al.; Synthetic Communications; vol. 4; (1974); p. 57

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys Patent; BASF; FR2232534; (1974); DE2400111; ; vol. 81; nb. 192884 View in Reaxys Yamazaki et al.; Tetrahedron Letters; (1967); p. 3317 View in Reaxys Le Guyader; Peltier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 253; (1961); p. 2544,2545 View in Reaxys Liljegren; Phytochemistry (Elsevier); vol. 10; (1971); p. 2661,2668 View in Reaxys Murray; Vaugham; Journal of the Chemical Society [Section] C: Organic; (1970); p. 2070,2073 View in Reaxys Neilson et al.; Journal of the Chemical Society; (1962); p. 371 View in Reaxys Cohen; Gray; Journal of Organic Chemistry; vol. 37; (1972); p. 741 View in Reaxys May et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 2274 View in Reaxys Schellenberg; Steinmetz; Helvetica Chimica Acta; vol. 52; (1969); p. 431 View in Reaxys Anderson; Way; Journal of the Chemical Society [Section] C: Organic; (1967); p. 1139 View in Reaxys Suter; Turner; Journal of the Chemical Society [Section] C: Organic; (1967); p. 2240 View in Reaxys Hazard; Tallec; Bulletin de la Societe Chimique de France; (1976); p. 433,437 View in Reaxys Bakke et al.; Acta Chemica Scandinavica (1947-1973); vol. 26; (1972); p. 355,361 View in Reaxys Paterson et al.; Tetrahedron Letters; (1977); p. 3973,3975 View in Reaxys Vainshtein et al.; Kinetics and Catalysis; vol. 10; (1969); p. 635,639 View in Reaxys Ayres; Gopalan; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 588 View in Reaxys Mc Cormick et al.; Journal of the American Chemical Society; vol. 84; (1962); p. 3711,3714 View in Reaxys Dunn; Prysiazniuk; Canadian Journal of Chemistry; vol. 39; (1961); p. 285,288 View in Reaxys Zeitler; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 340; (1965); p. 73,77 View in Reaxys Kuchtenko; Doklady Chemistry; vol. 132; (1960); p. 573; Doklady Akademii Nauk SSSR; vol. 132; (1960); p. 609 View in Reaxys Bentley; Chemistry and Industry (London, United Kingdom); (1973); p. 117 View in Reaxys Lingens; Goebel; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 342; (1965); p. 1,5 View in Reaxys Nagahara et al.; Chemical and Pharmaceutical Bulletin; vol. 24; (1976); p. 1197,1198-1200 View in Reaxys Yoshida et al.; Kogyo Kagaku Zasshi; vol. 65; (1962); p. 46 View in Reaxys Nakagawa et al.; Yakugaku Zasshi; vol. 97; (1977); p. 1253,1255; ; vol. 88; nb. 190270; (1978) View in Reaxys Patent; Hendrych et al.; CS140581; (1968); ; vol. 76; nb. 153356; (1972) View in Reaxys Biehl; Li; Journal of Organic Chemistry; vol. 31; (1966); p. 602 View in Reaxys Biehl et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 500 View in Reaxys Fields; Meyerson; Tetrahedron Letters; (1968); p. 1201 View in Reaxys Grinter et al.; Tetrahedron Letters; (1968); p. 3845

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys EXAMPLES General procedure for the synthesis of non-commercially available anthranilic acids A solution of the appropriate aniline (50.0 mmol) in acetic acid (30.0 mL) was heated to 45° C. Bromine (55.5 mmol, 2.8 mL) was then added dropwise at a rate to keep the temperature between 50-55° C. The temperature was held at 50° C. for 1.5 h.

The reaction was allowed to cool to ambient temperature and was poured into ice with stirring.

Sodium bisulfite (1.0 g) was added and stirred for 30 min.

The solution was extracted with ethyl acetate (2*50.0 mL).

The combined organic extracts were washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give a dark oil.

The oil was purified by flash chromatography (silica gel, 5-10percent ethyl acetate in hexanes) to give the aryl bromide as a light brown oil.

A solution of the aryl bromide (12.0 mmol) in N,N-dimethylformamide (8.0 mL) was stirred at ambient temperature.

Copper cyanide (15.0 mmol, 1.3 g) was added and the reaction was heated to 155° C. for 4 h.

The reaction was allowed to cool and poured into a solution of ethylene diamine (0.1 mL) in water (130.0 mL) and stirred for 30 min.

The solution was extracted with ethyl acetate (2*70.0 mL).

The organic extracts were combined and washed with saturated ammonium chloride and brine, dried with sodium sulfate and concentrated in vacuo.

The residue was then purified by flash chromatography (silica gel, 10percent ethyl acetate in hexane) to give the aryl cyanide as a orange oil.

To a solution of the aryl cyanide (1.5 mmol) in acetic acid (2.0 mL) was added 50percent sulfuric acid (6.0 mL), The reaction was heated to reflux for 2.5 h.

The reaction was allowed to cool to ambient temperature and poured into ice (50.0 g).

The solution was neutralized with potassium hydroxide (6M) and extracted with ethyl acetate (2*40.0 mL).

The combined organics were washed with brine and dried with sodium sulfate, filtered and dried in vacuo to a solid.

The solid was purified by flash chromatography (silica gel, 15percent ethyl acetate in methylene chloride to 8percent methanol in methylene chloride) to give the anthranilic acid as a white solid.

Patent; Lu, Tianbao; Lafrance III, Louis V.; Parks, Daniel J.; Milkiewicz, Karen L.; Calvo, Raul R.; Cummings, Maxwell D.; Kim, Alexander J.; Grasberger, Bruce L.; Carver JR., Theodore E.; US2003/109518; (2003); (A1) English View in Reaxys A. Amides Derived from the Following Monoaminocarboxylic Acids ...

15. Tyrosine 16. Valine 17. δ-Alanine 18. 4-Aminobutyric Acid Anthranilic Acid 20. 4-Aminobenzoic Acid 21. 3-Amino-2-naphthoic Acid 22. 4-Aminosalicylic acid ...

Patent; Schmitz, Robert A.; US6299892; (2001); (B1) English View in Reaxys 1 : 1,2-Dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester EXAMPLE 1 1,2-Dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester To a solution of 2,6-difluorobensonitril (42 g, 0.30 mol) in 150 ml of anhydrous methanol sodium methoxide (17.9 g, 0.33 mol) was slowly added at 30° C. After being heated under reflux for 1 hour, aqueous 40percent methylamine (133 ml, 1.2 mol) was added and the resulting solution refluxed for 4 days.

On cooling, a white solid, 2-methoxy-6-(methylamino)benso-nitrile, precipitated which was collected by filtration.

The precipitate was dissolved in an aqueous solution of ethylene glycol (500 ml) and potassium hydroxide (14 g).

The solution was refluxed at 150° C. over night, cooled to room temperature and the pH adjusted to 4 with conc. hydrochloric acid.

The anthranilic acid formed was collected by filtration, washed with water (50 ml) and dried under vacuum.

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Patent; Active Biotech AB; US6133285; (2000); (A) English View in Reaxys Exemplary amines and diamines useful in the invention are: ...

3-chloro-6-amino-4-methylbenzene-sulfonic acid 2-amino-5-methylbenzene sulfonic acid 2-methoxy-5-nitro-aniline 5-aminoisophthalic acid dimethyl ester 2-aminobenzoic acid 2-trifluoromethylaniline 3-amino-4-methoxybenzanilide Patent; Hoechst Celanese Corporation; US5176750; (1993); (A) English View in Reaxys II. Compounds containing acid groups, such as, carboxylic acids acetic acid propionic acid ... meta-phthalic acid para-phthalic acid salicylic acid hydroxybenzoic acid aminobenzoic acid Patent; Schering Aktiengesellschaft; US5501863; (1996); (A) English View in Reaxys As the compound of the formula (IV), the following are given: Aniline, o-, m- or p-toluidine, 2,4- or 2,5-dimethylaniline, 5-methyl-2-methoxyaniline, o-, m- or p-chloroaniline, aniline-2-, -3- or -4-sulfonic acid, ...

4-methoxyaniline-2-sulfonic acid, 4-chloroaniline-3-sulfonic acid, 5-acetylaminoaniline-2,4-disulfonic acid, anthranilic acid, 2-aminoterephthalic acid, m-aminobenzoic acid, 3- or 4-aminophthalic acid, p-aminobenzoic acid, 5-nitroanthranilic acid, 6-nitro-3-aminobenzoic acid, 5-nitro-2-aminoterephthalic acid, ...

Patent; Sumitomo Chemical Company, Limited; US4663440; (1987); (A) English View in Reaxys 1.1.1 : 1.1 The sodium salt is precipitated by the addition of 2,400 g of sodium hydroxide and isolated.

Patent; BASF Farben and Fasern AG; US4247296; (1981); (A) English View in Reaxys 2.2 : 2.

55 g of 2,4-dichloro-3-methyl-5-nitrobenzoic acid and 141.6 g of Na2 S2 O4 are boiled in a mixture of 440 ml of glycol monomethyl ether and 440 ml of water for 3 hours. 620 ml of 1/2-concentrated HCl are added to the still warm solution and the mixture is then boiled up once more.

After cooling to room temperature, the mixture is poured into 1.5 l of water and brought to pH 5 with sodium carbonate. 24.6 g of aminobenzoic acid are obtained.

Melting point: 202°-3°.

Patent; Bayer Aktiengesellschaft; US4762844; (1988); (A) English View in Reaxys As the compound of the formula (V), the following ones are given:

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Aniline, m-toluidine, o-toluidine, 2,5-dimethylaniline, o-anisidine, m-anisidine, 2,5-dimethoxyaniline, 5-methyl-2-methoxyaniline, anthranilic acid, 4-methyl-2-aminobenzoic acid, 3-acetylaminoaniline, m-ureidoaniline, 3-acetylamino-6-methylaniline, 3-acetylamino-6-methoxyaniline, 3-benzoylaminoaniline, 1-naphthylamine-6-sulfonic acid, ...

Patent; Sumitomo Chemical Company, Limited; US4663440; (1987); (A) English View in Reaxys Examples of such compounds are 2-aminobenzoic acid 3-aminobenzoic acid 4-aminobenzoic acid 4-methylaminobenzoic acid 3,5-diaminobenzoic acid 4-aminosalicylic acid 4-aminohippuric acid Patent; Amersham International plc; US4451451; (1984); (A) English View in Reaxys Products 3, 4 and 5 of Table I were prepared by combining ethanolic solutions of molar quantities of 2,4-dihydroxy-benzaldehyde and (3) anthranilic acid (4) p-aminobenzoic acid and (5) sulfanilic acid.

Patent; Henkel Kommanditgesellschaft Auf Aktien; US4828568; (1989); (A) English View in Reaxys derivatives thereof 2-amino-4,6-dinitrophenol 2-amino-4-sulpho-benzoic acid anthranilic acid 2-amino-6-nitro-4-tert. amyl-phenol 2-aminophenol-4-methylsulphone 5-nitro-2-aminophenol-4-methylsulphone 1-amino-2-hydroxynaphthalone-4-sulphonic acid Patent; Ciba-Geigy AG; US3941765; (1976); (A) English View in Reaxys Specific examples are: ...

5-nitro-2-aminophenol, 4.6-dichloro-2-aminophenol, 4,6-dinitro-2-aminophenol, 4-methyl-6-nitro-2-aminophenol, 4-chloro-5-nitro-2-aminoanisole, 4,5-dichloro-2-aminoanisole, 2-aminobenzoic acid, 4-nitro-2-aminobenzoic acid, 2-aminophenol-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, ...

Patent; BASF Aktiengesellschaft; US4052374; (1977); (A) English View in Reaxys 1.b : EXAMPLE 1

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

(b) 57.3 parts by volume of the solution thus obtained and to which 0.07 part of sulfamic acid has been added and 30.4 parts by volume of hypochlorite solution (containing 5.3 parts of sodium hypochlorite) are supplied continuously each hour by a metering pump to mixing means (mixing temperature 25° C) and reacted in an attached tubular reactor at 25° C. After a reaction period of 1.5 seconds in the reactor, during which the temperature rises to 43° C, the mixture has metered into it continuously each hour 17.1 parts by volume of 25percent by weight caustic soda solution in the reactor.

After another 4.5 seconds residence time in the reactor the temperature of the mixture has risen to 80° C. The alkali metal anthranilate solution containing alkali metal carbonate leaves the reactor as a clear pale solution.

The mixture is cooled to 20° C and adjusted with sulfuric acid to a pH of 4.3.

The mixture is filtered and the filter cake is washed with water and dried. 9.4 parts per hour (96.5percent of theory) of colorless anthranilic acid having a melting point of 145° C is obtained.

The space-time yield is 22.5 parts per hour per liter of reaction volume.

Patent; BASF Aktiengesellschaft; US4082749; (1978); (A) English View in Reaxys 13.b : EXAMPLE 13 (b) 3 parts of urea is added to 363 parts by volume of the solution thus obtained and the solution is cooled to -9° C. 452 parts by volume of hypochlorite solution (containing 75 parts of sodium hypochlorite) at -9° C is added rapidly to the mixture.

Then 105 parts by volume of 50percent by weight aqueous caustic soda solution is added all at once.

The temperature rises to 77° C. The clear pale solution is cooled to 20° C and adjusted to a pH of 4.3 with sulfuric acid.

The mixture is filtered and the filter cake is washed and dried. 124.5 parts (91percent of theory) of colorless anthranilic acid is obtained having a melting point of 144° to 145° C. Patent; BASF Aktiengesellschaft; US4082749; (1978); (A) English View in Reaxys which an aromatic diazonium salt, e.g. any of those mentioned in the above, or the following lists: (b) Aromatic amines containing a sulphonic or carboxylic acid group aniline-2,3 and 4-sulphonic acid ...

4-methoxyaniline-2-sulphonic acid 4-chloroaniline-3-sulphonic acid 5-acetylaminoaniline-2,4-disulphonic acid anthranilic acid 2-aminoterephthalic acid m-aminobenzoic acid 3- or 4-aminophthalic acid ...

Patent; Imperial Chemical Industries Limited; US4091021; (1978); (A) English View in Reaxys Exemplary amines and diamines useful in the invention are: ...

2-methoxy-5-nitro-aniline 5-aminoisophthalic acid dimethyl ester 2-aminobenzoic acid 2-trifluoromethylaniline ...

Patent; HOECHST CELANESE CORPORATION; EP592907; (1994); (A1) English View in Reaxys Representative but non-exhaustive examples of amines which can be alkoxylated according to the present invention are: aniline benzylamine hexadecylamine triphenylamine aminoacetic acid anthranilic acid cyclohexylamine

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

tert-octylamine ortho-phenylenediamine meta-phenylenediamine ...

Patent; Vista Chemical Company; US4540828; (1985); (A) English View in Reaxys Patent; Vista Chemical Company; US4568774; (1986); (A) English View in Reaxys Patent; Vista Chemical Company; US4593142; (1986); (A) English View in Reaxys These examples relate to the use of the following compounds: ...

4-nitrophthalic acid 3,5-diaminobenzoic acid o-nitrophenylpyruvic acid 3-nitro-1,9-naphthalic acid o-aminobenzoic acid 4-nitro-2-aminobenzoic acid p-hydroxybenzoic acid Patent; Burlington Industries, Inc.; US4111648; (1978); (A) English View in Reaxys Patent; Burlington Industries, Inc.; US4171954; (1979); (A) English View in Reaxys H 2N O

resin-bound 2-azidobenzoic acid HO

Rx-ID: 9376982 View in Reaxys 70/361 Yield 90 %

Conditions & References Stage 1: With aluminium, nickel dichloride, Time= 30h, T= 20 °C Stage 2: With trifluoroacetic acid Kamal, Ahmed; Reddy, K. Laxma; Devaiah; Reddy, G. Suresh Kumar; Tetrahedron Letters; vol. 44; nb. 25; (2003); p. 4741 - 4745 View in Reaxys H 2N O

resin-bound 2-nitrobenzoic acid HO

Rx-ID: 9376984 View in Reaxys 71/361 Yield 80 %

Conditions & References Stage 1: With aluminium, nickel dichloride, Time= 1.16667h, T= 20 °C Stage 2: With trifluoroacetic acid Kamal, Ahmed; Reddy, K. Laxma; Devaiah; Reddy, G. Suresh Kumar; Tetrahedron Letters; vol. 44; nb. 25; (2003); p. 4741 - 4745 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

N

O

OH

H 2N O

N N HO

Rx-ID: 9678408 View in Reaxys 72/361 Yield

Conditions & References

88 %

With ammonium formate, nickel in methanol, Time= 0.25h, T= 20 °C Gowda, D. Channe; Gowda, Shankare; Abiraj; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 7; (2003); p. 1774 - 1776 View in Reaxys

H 2N

H 2N O

HO NH

O HO

O

HO

Rx-ID: 23858795 View in Reaxys 73/361 Yield

Conditions & References 4-octyl anthranilic Acid (4-octyl-2-aminobenzoic Acid) 4-octyl anthranilic Acid (4-octyl-2-aminobenzoic Acid) Method based on that of L. A. Paquette et al. J.Am.Chem.Soc. 99, 3734 (1981) A solution of 1-bromo-4-octylbenzene (9.9 g, 36 mmol) in sulfuric acid (20 ml) was cooled in an ice bath.

To this was added nitric acid (1.44 ml, 36 mmol).

The ice bath was removed and the mixture stirred at room temperature for 20 minutes.

A further portion of nitric acid was added (0.07 ml, 1.75 mmol), stirring being continued for a further 20 min.

The mixture was poured into aqueous potassium carbonate, which was extracted with ethyl acetate.

The organic extract was washed with saturated aqueous potassium carbonate, water and brine then dried (MgSO4) and concentrated.

Purification of the crude product by flash chromatography (1percent EtOAc/hexane) removed the unwanted (major) regioisomer and afforded the desired material as a yellow oil (1.7 g, 5.4 mmol).

The substrate (1.7 g, 5.4 mmol), copper (I) cyanide (0.533 g, 5.9 mmol) and pyridine (20 ml) were refluxed at 150° C. for 2 days.

Concentration in vacuo and purification by flash chromatography (10percent to 20percent EtOAc/hexane) gave the desired material as a brown oil (739 mg, 2.8 mmol) The substrate (694 mg, 2.7 mmol) was heated at 150° C. in a mixture of water (2 ml), AcOH (1 ml) and sulfuric acid (1 ml) for 2 days.

The mixture was extracted with ethyl acetate, the organic phase being washed with water (*2), dried (Na2SO4) and concentrated to give the desired material (744 mg, 2.7 mmol).

The starting material (744 mg, 2.7 mmol) was dissolved in ethanol (10 ml) and to this was added a slurry of 10percent palladium on charcoal (40 mg) in ethanol (4 ml).

The flask was flushed with nitrogen then hydrogen (1 atm) after which stirring was maintained overnight.

Further portions of catalyst (5 mg and 25 mg) were added, the reaction being complete after a further 24 h.

The reaction mixture was filtered through celite, thoroughly rinsing with methanol and ethyl acetate.

Concentration gave the anthranilic acid (597 mg, 2.4 mmol) of sufficient purity for use without further purification; H δ (400 MHz, CDCl3) 0.79-0.81 (3H, m, Me), 1.12-1.36 (10H, m, 5*CH2), 1.52 (2H, br.s, ArCH2CH2), 2.45 (2H, br.s, ArCH2), 6.42 (2H, br.s, 2*ArH), 7.74 (1H, br.s, ArH); m/z (ES+) 250 (MH+).

Patent; Hodson, Harold Francis; Downham, Robert; Mitchell, Timothy John; Carr, Beverley Jane; Dunk, Christopher Robert; Palmer, Richard Michael John; US2003/27821; (2003); (A1) English View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N H 2N

O

O

O

N

O N

O

OH

O HO

O

Rx-ID: 9072692 View in Reaxys 74/361 Yield

Conditions & References With water, T= 50 °C , pH= 2.2, Kinetics, Further Variations: pH-values Fife, Thomas H.; Singh, Randhir; Bembi, Ramesh; Journal of Organic Chemistry; vol. 67; nb. 10; (2002); p. 3179 - 3183 View in Reaxys O

NH 2

H 2N

F

F

O

O F

F

HO F

F

HO

Rx-ID: 9073066 View in Reaxys 75/361 Yield

Conditions & References With water, T= 50 °C , pH= 3.45, Kinetics, Further Variations: pH-values Fife, Thomas H.; Singh, Randhir; Bembi, Ramesh; Journal of Organic Chemistry; vol. 67; nb. 10; (2002); p. 3179 - 3183 View in Reaxys H 2N

O H 2N

HO N

O

HO

O

O

O

O

O

OH

O HO

Rx-ID: 9182409 View in Reaxys 76/361 Yield

Conditions & References With perchloric acid, ozone in water, T= 25 °C , pH= 5.5, Kinetics Andreozzi, Roberto; Marotta, Raffaele; Pinto, Gabriele; Pollio, Antonino; Water research; vol. 36; nb. 11; (2002); p. 2869 2877 View in Reaxys

H N

OH O

O

OH H 2N

H N

O

N

O

HO

O O

HO

O

Rx-ID: 9303900 View in Reaxys 77/361 Yield

Conditions & References With potassium tert-butylate in N,N-dimethyl-formamide, Time= 6h, T= 25 °C , Product distribution, Further Variations: solvent dependence

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Czaun, Miklos; Speier, Gabor; Tetrahedron Letters; vol. 43; nb. 34; (2002); p. 5961 - 5963 View in Reaxys

Br H N

OH O

Br Br

O

OH H 2N O

N

H N

O

HO

O O

HO

O

Rx-ID: 9331163 View in Reaxys 78/361 Yield

Conditions & References With potassium tert-butylate, oxygen in N,N-dimethyl-formamide, Time= 6h, T= 25 °C , Product distribution, Further Variations: solvent dependence Czaun, Miklos; Speier, Gabor; Tetrahedron Letters; vol. 43; nb. 34; (2002); p. 5961 - 5963 View in Reaxys

O

O

H N

N

O OH O

O

H 2N

O O

O

N H

HO HO

O

O

OH

Rx-ID: 9353848 View in Reaxys 79/361 Yield

Conditions & References With potassium tert-butylate, oxygen in N,N-dimethyl-formamide, Time= 6h, T= 25 °C , Product distribution, Further Variations: solvent dependence Czaun, Miklos; Speier, Gabor; Tetrahedron Letters; vol. 43; nb. 34; (2002); p. 5961 - 5963 View in Reaxys H 2N

O NH 2

O

HO

Rx-ID: 24005931 View in Reaxys 80/361 Yield

Conditions & References 70 : 8-Fluoro4,4-dimethyl-dihydro-benzo [d] [1,3]oxazin-2-one EXAMPLE 70 8-Fluoro4,4-dimethyl-dihydro-benzo [d] [1,3]oxazin-2-one

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

N-(tert-Butoxycarbonylamino)-3-fluorobenzoic acid (Takagishi et al. Synlett 4, 360-2 (1992); mp 159-161° C.) was deprotected using trifluoroacetic acid to give o-amino benzoic acid which was treated with methylmagnesium bromide to afford o-amino dimethyl carbinol.

Patent; Zhang, Puwen; Terefenko, Eugene A.; Fensome, Andrew; Wrobel, Jay E.; Fletcher III, Horace; Zhi, Lin; Jones, Todd K.; Edwards, James P.; Tegley, Christopher M.; US2002/49204; (2002); (A1) English View in Reaxys 57 : 3-Fluoro-5-(8-fluoro-4,4-dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)benzonitrile EXAMPLE 57 3-Fluoro-5-(8-fluoro-4,4-dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)benzonitrile N-(tert-Butoxycarbonylamino)-3-fluorobenzoic acid (Takagishi et al. Synlett 4, 360-2 (1992), mp 159-161° C.) was deprotected using trifluoroacetic acid to give o-amino benzoic acid, which was then treated with methylmagnesium bromide to afford oamino dimethyl carbinol.

Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6436929; (2002); (B1) English View in Reaxys 70 : 8-Fluoro4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-one EXAMPLE 70 8-Fluoro4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-one N-(tert-Butoxycarbonylamino)-3-fluorobenzoic acid (Takagishi et al. Synlett 4, 360-2 (1992); mp 159-161° C.) was deprotected using trifluoroacetic acid to give o-amino benzoic acid which was treated with methylmagesium bromide to afford o-amino dimethyl carbinol.

Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6444668; (2002); (B1) English View in Reaxys

O O

O

O

O

H 2N O

H N

N N H

O

H 2N

O O

NH 2

HO

O

Rx-ID: 24125896 View in Reaxys 81/361 Yield 78%

Conditions & References 7 : Synthesis of 2-amino Benzoic Acid Oligomers as Protection Groups THF was removed in vacuo, the product filtered, washed with water, and dried to a give white solid.

Yield 78percent.

Benzyl amine was acylated of in the presence of 2-(2-aminobenzoylamino)benzoic acid methyl ester (UCP-dimer).

2-(2-Aminobenzoylamino)benzoic acid methyl ester (0.089 mmol) and benzyl amine (0.089 mmol) were dissolved in DMF (1 mL). Boc-Ala-OSu (0.132 mmol, 1.5 equiv) and DIPEA (0.265 mmol, 3 equiv) were added, mixed thoroughly, and left at room temperature for 40 min.

The reaction was monitored TLC (silica; eluent: ethyl acetate:petroleum spirit (1:3)).

After the reaction time, it was found by TLC and ES-MS analysis that the benzyl amine was completely acylated and the starting dimeric UCP-protecting group was unreacted.

The presence of the Boc-alanine acylated derivative of the dimeric protecting group was not observed.

With N-ethyl-N,N-diisopropylamine, 2-(2-aminobenzoylamino)benzoic acid methyl ester (UCP-dimer) in N,N-dimethyl-formamide Patent; Meldal, Morten Peter; Miranda, Leslie Philip; US2002/146684; (2002); (A1) English View in Reaxys O NH

HN O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O H 2N

O

O

OH

O

HO

OH

O

HO

OH

N O

OH

OH

HO

O

O

Rx-ID: 8904447 View in Reaxys 82/361 Yield

Conditions & References With air, water, titanium(IV) oxide, T= 21.85 °C , UV-irradiation, Kinetics, Further Variations: Reagents Vautier, Manon; Guillard, Chantal; Herrmann, Jean-Marie; Journal of Catalysis; vol. 201; nb. 1; (2001); p. 46 - 59 View in Reaxys 2 O

O

O

Na +

S

NH

O– –O

HN

S O

O

O

O

H 2N

O

O

OH

O

HO

OH

OH

O

HO

N

O

OH

OH

HO

O O

Rx-ID: 8924783 View in Reaxys 83/361 Yield

Conditions & References With air, water, titanium(IV) oxide, T= 21.85 °C , UV-irradiation, Kinetics, Further Variations: Reagents Vautier, Manon; Guillard, Chantal; Herrmann, Jean-Marie; Journal of Catalysis; vol. 201; nb. 1; (2001); p. 46 - 59 View in Reaxys

Cl H 2N

O

O

O

O

Cl

HO

Rx-ID: 8622861 View in Reaxys 84/361 Yield

Conditions & References With sodium hydroxide in methanol, T= 25 °C , Condensation, Cyclization Marcinow, Zbigniew; Rabideau, Peter W.; Journal of Organic Chemistry; vol. 65; nb. 16; (2000); p. 5063 - 5065 View in Reaxys

O

O

H 2N

HO H

O

N

O N

O

HO O

O

O

Rx-ID: 8773316 View in Reaxys 85/361 Yield

Conditions & References With 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, Time= 48h, T= 20 °C Haddadin, Makhluf J.; Nazer, Musa Z.; Heterocycles; vol. 53; nb. 10; (2000); p. 2221 - 2224

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys

NH 2

O

NH 2

H

H 2N

NH 2

HO

O

Cl

HO

H

O

HO

O

Rx-ID: 5303369 View in Reaxys 86/361 Yield

Conditions & References With Pseudomonas florescens kinureninase, pyridoxal 5'-phosphate in phosphate buffer, T= 25 °C , pH= 7.8, Hydrolysis, Enzyme kinetics, Further Variations: Reagents Cyr, Lakshmi V.; Newton, M. Gary; Phillips, Robert S.; Bioorganic and Medicinal Chemistry; vol. 7; nb. 8; (1999); p. 1497 1503 View in Reaxys

NH 2

O

NH 2

H

H 2N

NH 2

HO

O

Cl

HO

H

O

HO

O

Rx-ID: 5303370 View in Reaxys 87/361 Yield

Conditions & References With Pseudomonas florescens kinureninase, pyridoxal 5'-phosphate in phosphate buffer, T= 25 °C , pH= 7.8, Hydrolysis, Enzyme kinetics Cyr, Lakshmi V.; Newton, M. Gary; Phillips, Robert S.; Bioorganic and Medicinal Chemistry; vol. 7; nb. 8; (1999); p. 1497 1503 View in Reaxys

O

H 2N H 2N

O

N

O

NH 2

HN

HN

N

O HO

O

O

O

Rx-ID: 5318401 View in Reaxys 88/361 Yield

Conditions & References

50 %, 12 %, With water, Ring cleavage, Dimerization; Trimerization 22 % Chiu, Shao-Jung; Chou, Chin-Hsing; Tetrahedron Letters; vol. 40; nb. 52; (1999); p. 9271 - 9272 View in Reaxys H N

O

O

Fmoc amino acid derivatized Wang-resin

O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

isopentenylnitrit HO

Rx-ID: 16040155 View in Reaxys 89/361 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / 550 °C / 0.01 Torr 2: 12 percent / H2O With water, 1: Ring cleavage / 2: Ring cleavage Chiu, Shao-Jung; Chou, Chin-Hsing; Tetrahedron Letters; vol. 40; nb. 52; (1999); p. 9271 - 9272 View in Reaxys

NH 2 N O

N

O

HO

O

OH

NH 2

H N

O

N O HO

N

P O

O

O

O

O

O

OH

HO P O O

NH 2 N N

N

N

O

HO

OH

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O N

HO

O

NH 2 O

N

HO

NH 2

N

O

O

N

OH

HO

O

O P

N

O

NH 2

O

O

OH O

HO

P

N

O

N

NH 2

O

H 2N

O

N

O

O

OH O

O HO

P O HO

OH

O

N

P O

O

NH 2

N

N

N HO

N

HO

O

O

O

N O

NH 2

O

NH 2

N

N

OH

NH 2

Rx-ID: 4984646 View in Reaxys 90/361 Yield

Conditions & References With sodium hydroxide in water, acetonitrile, Time= 3h, T= 38 °C , pH 8.6, Yield given. Yields of byproduct given. Title compound not separated from byproducts Nawrot; Sprinzl; Nucleosides and Nucleotides; vol. 17; nb. 4; (1998); p. 815 - 829 View in Reaxys

H N

O

H 2N

HO O

NH

N H OH

HO

O

Rx-ID: 5066172 View in Reaxys 91/361 Yield

Conditions & References With potassium hydroxide, Time= 120h, T= 20 °C , Hydrolysis Ukrainets; Taran; Sidorenko; Gorokhova; Chemistry of Heterocyclic Compounds; vol. 33; nb. 11; (1997); p. 1334 - 1336 View in Reaxys H N

O

H 2N O

isopentenylnitrit NH 2 HO

OH

Rx-ID: 16566476 View in Reaxys 92/361 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / 730.5 h / 20 °C 2: aq. KOH / 120 h / 20 °C With potassium hydroxide, 1: Dimerization / 2: Hydrolysis Ukrainets; Taran; Sidorenko; Gorokhova; Chemistry of Heterocyclic Compounds; vol. 33; nb. 11; (1997); p. 1334 - 1336 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

H 2N

O Cl

O

H

NH 2

HO

Rx-ID: 4571861 View in Reaxys 93/361 Yield

Conditions & References With sodium hydroxide in ethanol, Time= 3h, Heating, pH 14 Van Liemt; Beijersbergen Van Henegouwen; Van Rijn; Lugtenburg; Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands; vol. 115; nb. 10; (1996); p. 431 - 437 View in Reaxys

NH 2

O

H 2N O

Si

CS2

O

HO

Rx-ID: 17613868 View in Reaxys 94/361 Yield

Conditions & References Reaction Steps: 2 1: CF3COOH / hexane / 4 h / Heating 2: aq. NaOH / ethanol / 3 h / Heating; pH 14 With sodium hydroxide, trifluoroacetic acid in ethanol, hexane Van Liemt; Beijersbergen Van Henegouwen; Van Rijn; Lugtenburg; Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands; vol. 115; nb. 10; (1996); p. 431 - 437 View in Reaxys H 2N

O O

NH 2 HO HO

Rx-ID: 24589621 View in Reaxys 95/361 Yield

Conditions & References 4 : EXAMPLE 4 EXAMPLE 4 This example illustrates synthesis of a dye useful at pH levels of 9 to 11.

The dye is synthesised from diazotized p-aminobenzoic acid and APB. 100.12 mg of p-aminobenzoic acid was dissolved in 1 ml of water.

Upon chilling the solution, the aminobenzoic acid crystallized.

The crystals partially dissolved when the solution was brought to 0.6N in HCl. in water Patent; Russell; Anthony P.; US5512246; (1996); (A) English View in Reaxys N N+ O

HO

N

â&#x20AC;&#x201C;O

O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N

HO

O

O O

O

O

O HO

N H O

HO HO

O

OH

Rx-ID: 4064626 View in Reaxys 96/361 Yield

Conditions & References Time= 48h, Ambient temperature, acids were separated as methyl esters (methylated by CH2N2), Product distribution, Mechanism Christopher Buxton; Fensome, Mark; Heaney, Harry; Mason, Kenneth G.; Tetrahedron; vol. 51; nb. 10; (1995); p. 2959 2968 View in Reaxys

N N+

H 2N O O

N

–O

HO HO

O

Rx-ID: 4112134 View in Reaxys 97/361 Yield

Conditions & References Time= 48h, Product distribution, Mechanism Christopher Buxton; Fensome, Mark; Heaney, Harry; Mason, Kenneth G.; Tetrahedron; vol. 51; nb. 10; (1995); p. 2959 2968 View in Reaxys

O N O O H 2N

H 2N

O O

O

N O

HO

HO

N

O

O

Rx-ID: 4159810 View in Reaxys 98/361 Yield

Conditions & References in benzene, T= 340 °C , in sealed tube; other solvent (neat), Product distribution, Kinetics, Rate constant Oxley, Jimmie C.; Smith, James L.; Ye, Hong; McKenney, Robert L.; Bolduc, Paul R.; Journal of Physical Chemistry; vol.

99; nb. 23; (1995); p. 9593 - 9602 View in Reaxys

OH H 2N

O

H 2N O

O N

HO

HO

O

Rx-ID: 2021175 View in Reaxys 99/361 Yield 59 %, 20 %

Conditions & References With hydrogenchloride, samarium in methanol, Time= 0.166667h, Ambient temperature Kamochi; Kudo; Chemical and Pharmaceutical Bulletin; vol. 42; nb. 2; (1994); p. 402 - 404 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

27 %, 48 %

With hydrogenchloride, ytterbium in methanol, Time= 0.166667h, Ambient temperature Kamochi; Kudo; Chemical and Pharmaceutical Bulletin; vol. 42; nb. 2; (1994); p. 402 - 404 View in Reaxys H 2N

H N

O

HO

Rx-ID: 2433036 View in Reaxys 100/361 Yield

Conditions & References With disodium hydrogenphosphate, potassium dihydrogenphosphate, ethylene glycol monolaurate, Pseudomonas stutzeri, magnesium sulfate, iron(II) sulfate, Time= 96h, T= 30 °C , microbial transformation, various conditions, Product distribution Hisatsuka, Kenichi; Sato, Mikio; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 1; (1994); p. 213 - 214 View in Reaxys

OH H 2N

N

N

N

N

O

HO

OH

HO

OH

Rx-ID: 1556422 View in Reaxys 101/361 Yield

Conditions & References

13 %, 27 %, With Pseudomonas putida 27 %, 33 % Boyd, Derek R.; McMordie, R. Austin S.; Porter, H. Patricia; Dalton, Howard; Jenkins, Richard O.; Howarth, Oliver W.; Journal of the Chemical Society, Chemical Communications; (1987); p. 1722 - 1724 View in Reaxys 11 mg, 23 mg, 22 mg, 32 %

biotransformation by Pseudomonas putida UV4, Further byproducts given

11 mg, 23 mg, 22 mg, 32 mg

biotransformation by Pseudomonas putida UV4, Further byproducts given

Boyd, Derek R.; Sharma, Narain D.; Dorrity, Michael R. J.; Hand, Mark V.; McMordie, R. Austin S.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1993); p. 1065 - 1072 View in Reaxys

Boyd, Derek R.; Sharma, Narain D.; Dorrity, Michael R. J.; Hand, Mark V.; McMordie, R. Austin S.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1993); p. 1065 - 1072 View in Reaxys

N

OH

OH

H 2N

N N

OH

N HO

O

N

HO HO

OH

Rx-ID: 1556423 View in Reaxys 102/361 Yield 11 mg, 23 mg, 22 mg, 32 mg

Conditions & References biotransformation by Pseudomonas putida UV4, with isoquinoline, quinoxaline and quinazoline, Mechanism Boyd, Derek R.; Sharma, Narain D.; Dorrity, Michael R. J.; Hand, Mark V.; McMordie, R. Austin S.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1993); p. 1065 - 1072

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys O

OH H 2N

H N

O

O

HO

Rx-ID: 1630541 View in Reaxys 103/361 Yield

Conditions & References

90 %

With sulfuric acid in water, various aqueous milieus, Product distribution Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

79 %

With sulfuric acid in methanol, Ambient temperature Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys O O

O

OH

N

H 2N

H N

O

O

O

HO

Rx-ID: 2019406 View in Reaxys 104/361 Yield

Conditions & References

58 %, 36 %

With disodium hydrogenphosphate, sodium dihydrogenphosphate, Glyoxilic acid in methanol, water, Time= 48h, T= 50 °C Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys O

OH

OH H 2N

HN

O

H N

O

O

HO HO

Rx-ID: 2160401 View in Reaxys 105/361 Yield

Conditions & References

21 %, 41 %

With Glyoxilic acid in water, Time= 18h, T= 40 °C Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys OH

O

H 2N O

N N

HO

N

Rx-ID: 3454864 View in Reaxys 106/361 Yield 37 %

Conditions & References With potassium hydroxide, aluminum nickel in methanol, Time= 18h, Ambient temperature

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Gross, Margaret L.; Blank, David H.; Welch, Willard M.; Journal of Organic Chemistry; vol. 58; nb. 8; (1993); p. 2104 2109 View in Reaxys O O

O

OH

N

H 2N

HO

H N

O

O

O

O O

HO

Rx-ID: 3741965 View in Reaxys 107/361 Yield

Conditions & References

58 %, 36 %

With disodium hydrogenphosphate, sodium dihydrogenphosphate in methanol, water, Time= 48h, T= 50 °C Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

58 %, 36 %

With disodium hydrogenphosphate, sodium dihydrogenphosphate in methanol, water, Time= 48h, T= 50 °C , other 2-nitrosobenzoic acid derivatives, Mechanism, Product distribution Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys O

OH

OH H 2N

HN

HO

O

H N

O

O

O

O HO HO

Rx-ID: 3742001 View in Reaxys 108/361 Yield

Conditions & References

21 %, 41 %

in water, Time= 18h, T= 40 °C Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys OH H 2N

H 2N

O O

H N

O

N H HO

O

HO

OH

Rx-ID: 3845316 View in Reaxys 109/361 Yield 9 %, 28 %, 37 %

Conditions & References With samarium diiodide, water in tetrahydrofuran, Time= 0.0333333h, Ambient temperature Kamochi, Yasuko; Kudo, Tadahiro; Chemistry Letters; nb. 9; (1993); p. 1495 - 1498 View in Reaxys

H 2N

NH O

O

O

4-amino-2.6-dioxy-pyridine HO

Rx-ID: 19309199 View in Reaxys 110/361 Yield

Conditions & References Reaction Steps: 2 1: 60 percent / 0.5 M CH3CO2H, 0.5 M CH3CO2Na / methanol; H2O / 24 h / 40 °C 2: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

With sulfuric acid, sodium acetate, acetic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys O N O

o-nitroso-benzoic acid-ester

HO H 2N O

4-amino-2.6-dioxy-pyridine HO

Rx-ID: 19313466 View in Reaxys 111/361 Yield

Conditions & References Reaction Steps: 4 1: 36 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / H2O / 2 h / 40 °C 2: 91 percent / conc. H2SO4 / methanol 3: 60 percent / 0.5 M CH3CO2H, 0.5 M CH3CO2Na / methanol; H2O / 24 h / 40 °C 4: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid, sodium acetate, acetic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys O O

N

H 2N O

4-amino-2.6-dioxy-pyridine

O

HO

Rx-ID: 19313484 View in Reaxys 112/361 Yield

Conditions & References Reaction Steps: 2 1: 58 percent / glyoxylic acid, 0.25 M NaH2PO4, 0.25 M Na2HPO4 / methanol; H2O / 48 h / 50 °C 2: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid, Glyoxilic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys Reaction Steps: 2 1: 58 percent / NaH2PO4, Na2HPO4 / methanol; H2O / 48 h / 50 °C / other 2-nitrosobenzoic acid derivatives 2: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

OH

O

Fmoc-D-Phe Wang resin

O N O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

4-amino-2.6-dioxy-pyridine HO

Rx-ID: 19313522 View in Reaxys 113/361 Yield

Conditions & References Reaction Steps: 5 1: 91 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / electrochemical reaction 2: 36 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / H2O / 2 h / 40 °C 3: 91 percent / conc. H2SO4 / methanol 4: 60 percent / 0.5 M CH3CO2H, 0.5 M CH3CO2Na / methanol; H2O / 24 h / 40 °C 5: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid, sodium acetate, acetic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys O O

O N

H 2N O

4-amino-2.6-dioxy-pyridine

O

HO

Rx-ID: 19314738 View in Reaxys 114/361 Yield

Conditions & References Reaction Steps: 3 1: 55 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / electrochemical reaction 2: 58 percent / glyoxylic acid, 0.25 M NaH2PO4, 0.25 M Na2HPO4 / methanol; H2O / 48 h / 50 °C 3: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid, Glyoxilic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys Reaction Steps: 2 1: 55 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / electrochemical reaction 2: 36 percent / glyoxylic acid, 0.25 M NaH2PO4, 0.25 M Na2HPO4 / methanol; H2O / 48 h / 50 °C With disodium hydrogenphosphate, sodium dihydrogenphosphate, Glyoxilic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys Reaction Steps: 3 1: 55 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / electrochemical reaction 2: 58 percent / NaH2PO4, Na2HPO4 / methanol; H2O / 48 h / 50 °C / other 2-nitrosobenzoic acid derivatives 3: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys Reaction Steps: 2 1: 55 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / electrochemical reaction 2: 36 percent / NaH2PO4, Na2HPO4 / methanol; H2O / 48 h / 50 °C / other 2-nitrosobenzoic acid derivatives With disodium hydrogenphosphate, sodium dihydrogenphosphate in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH H 2N HN O O

4-amino-2.6-dioxy-pyridine HO

HO

Rx-ID: 19316839 View in Reaxys 115/361 Yield

Conditions & References Reaction Steps: 2 1: 21 percent / glyoxylic acid / H2O / 18 h / 40 °C 2: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With sulfuric acid, Glyoxilic acid in water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys Reaction Steps: 2 1: 21 percent / H2O / 18 h / 40 °C 2: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With sulfuric acid in water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

O O

O H 2N

N O

4-amino-2.6-dioxy-pyridine

N HO

Rx-ID: 19317069 View in Reaxys 116/361 Yield

Conditions & References Reaction Steps: 3 1: 75 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / electrochemical reaction 2: 55 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / methanol; H2O / 17 h / 60 °C 3: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

O O

H 2N

N O

4-amino-2.6-dioxy-pyridine

N HO

Rx-ID: 19326975 View in Reaxys 117/361 Yield

Conditions & References Reaction Steps: 2 1: 55 percent / 0.25 M NaH2PO4, 0.25 M Na2HPO4 / methanol; H2O / 17 h / 60 °C 2: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With disodium hydrogenphosphate, sodium dihydrogenphosphate, sulfuric acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Br H 2N O

N

4-amino-2.6-dioxy-pyridine

N HO

N

Rx-ID: 19330620 View in Reaxys 118/361 Yield

Conditions & References Reaction Steps: 2 1: 1) sec-BuLi / 1) ether, hexane, 30 min, -78 deg C, 2) -78 deg C to r.t.

2: 37 percent / 1M KOH, Al-Ni alloy / methanol / 18 h / Ambient temperature With potassium hydroxide, aluminum nickel, sec.-butyllithium in methanol Gross, Margaret L.; Blank, David H.; Welch, Willard M.; Journal of Organic Chemistry; vol. 58; nb. 8; (1993); p. 2104 2109 View in Reaxys O

OH

OH O

N

H 2N O

4-amino-2.6-dioxy-pyridine HO

Rx-ID: 19331022 View in Reaxys 119/361 Yield

Conditions & References Reaction Steps: 3 1: 91 percent / conc. H2SO4 / methanol 2: 60 percent / 0.5 M CH3CO2H, 0.5 M CH3CO2Na / methanol; H2O / 24 h / 40 °C 3: 90 percent / 1 N H2SO4 / H2O / various aqueous milieus With sulfuric acid, sodium acetate, acetic acid in methanol, water Guilbaud-Criqui, A.; Moinet, C.; Bulletin de la Societe Chimique de France; vol. 130; nb. 2; (1993); p. 164 - 172 View in Reaxys

H 2N

in addition to 4-bromo-aniline; 2:2.4dibromo-anilin; 3: aniline Br

H 2N O

4-amino-2.6-dioxy-pyridine HO

Rx-ID: 19349574 View in Reaxys 120/361 Yield

Conditions & References Reaction Steps: 3 1: 1) conc. HCl, NaNO2, 2) 1M KOH / 1) water, 10 min, ice bath, 2) 30 min, ice bath 2: 1) sec-BuLi / 1) ether, hexane, 30 min, -78 deg C, 2) -78 deg C to r.t.

3: 37 percent / 1M KOH, Al-Ni alloy / methanol / 18 h / Ambient temperature With hydrogenchloride, potassium hydroxide, aluminum nickel, sec.-butyllithium, sodium nitrite in methanol Gross, Margaret L.; Blank, David H.; Welch, Willard M.; Journal of Organic Chemistry; vol. 58; nb. 8; (1993); p. 2104 2109 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

N

O

H 2N O

O

H 2N O

NH

H N

O

H 2N NH

N

N

O

N

HN N

OH

HO

HN

Rx-ID: 3392530 View in Reaxys 121/361 Yield

Conditions & References

5.3 %, 25.8 %, 24.8 %, 31.8 %

Time= 2h, T= 150 - 155 °C Ukrainets, I. V.; Bezuglyi, P. A.; Treskach, V. I.; Turov, A. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 28; nb. 2; (1992); p. 198 - 200; Khimiya Geterotsiklicheskikh Soedinenii; nb. 2; (1992); p. 239 - 241 View in Reaxys O

N

O N

N

O

O

H 2N H 2N

N

H 2N

O

H 2N

O O

HO

O

Rx-ID: 3917447 View in Reaxys 122/361 Yield

Conditions & References

100.0 (unit not given), 15.1 (unit not given), 27.5 (unit not given), 31.5 (unit not given), 60.9 (unit not given), 11.0 (unit not given)

T= 343 °C , thermolysis in supercritical benzene; other temperature, pressure; primary H/D kinetic-isotope effect in benzene-d6 and o-nitrotoluene-d3; inter- and intramolecular decomposition, Kinetics, Mechanism, Product distribution Minier, Leanna M.; Brower, Kay R.; Oxley, Jimmie C.; Journal of Organic Chemistry; vol. 56; nb. 10; (1991); p. 3306 - 3314 View in Reaxys

HO

H 2N

O

O

O

OH HO

OH

HO HO

OH

H

HO

H 2N

Rx-ID: 1733745 View in Reaxys 123/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References

11.1 %

Time= 96h, T= 31.5 °C , auxotrophic mutant FT-1 derived from mFP-restistant wild-type strain MF358 of Brevibacterium lactofermentum; production medium SM-3, Yields of byproduct given Ito; Sakurai; Tanaka; Sato; Enei; Agricultural and biological chemistry; vol. 54; nb. 3; (1990); p. 699 - 705 View in Reaxys Time= 96h, T= 31.5 °C , auxotrophic mutant FT-6 derived from mFP-restistant wild-type strain MF358 of Brevibacterium lactofermentum; production medium SM-3, Yield given. Yields of byproduct given Ito; Sakurai; Tanaka; Sato; Enei; Agricultural and biological chemistry; vol. 54; nb. 3; (1990); p. 699 - 705 View in Reaxys

HO

H 2N

O

O

O

O

OH HO

OH

HO HO

HO

H

H

HO

H 2N

H 2N

OH

Rx-ID: 1733746 View in Reaxys 124/361 Yield

Conditions & References Time= 72h, T= 31.5 °C , wild-type strain transformant AJ12036/pAR2 of Brevibacterium lactofermentum; production medium SM-3, Yield given. Yields of byproduct given Ito; Sato; Matsui; Sano; Nakamori; Tanaka; Enei; Agricultural and biological chemistry; vol. 54; nb. 3; (1990); p. 707 - 713 View in Reaxys

HO

NH

O

NH

OH

HO

HO

H H 2N

HO

O HO

H 2N

NH

OH

O

OH HO

HO

O

OH

HO

Rx-ID: 2430105 View in Reaxys 125/361 Yield

Conditions & References With ethylenediaminetetraacetic acid, oxygen, iron(II) sulfate, ascorbic acid in water, Time= 2h, T= 30 - 32 °C , biomimetic hydroxylation, pH 6.7, Product distribution Chakraborty; Roy; Rakshit; Journal of the Indian Chemical Society; vol. 66; nb. 8-10; (1989); p. 699 - 702 View in Reaxys

O

H 2N

OH HO

NH

H

NH

HO

N H

HO

O HO

H 2N

NH

OH

O

OH HO

HO

O

OH

HO

Rx-ID: 3830109 View in Reaxys 126/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With ethylenediaminetetraacetic acid, oxygen, iron(II) sulfate, ascorbic acid in water, Time= 2h, T= 30 - 32 °C , biomimetic hydroxylation, pH 6.7, Product distribution Chakraborty; Roy; Rakshit; Journal of the Indian Chemical Society; vol. 66; nb. 8-10; (1989); p. 699 - 702 View in Reaxys

N

O

OH

H 2N O

N

N

NH 2

N HO

Rx-ID: 3958760 View in Reaxys 127/361 Yield

Conditions & References With potassium phosphate buffer, T= 25 °C , study of the enzymatic reduction of CDMAB by Bacillus Diaphorase in presence of NADH, kinetics of the process was followed, Product distribution, Rate constant Yatome, Chizuko; Ogawa, Toshihiko; Ogawa, Toshihiko; Hayashi, Hideki; Bulletin of the Chemical Society of Japan; vol.

62; nb. 4; (1989); p. 1123 - 1126 View in Reaxys

H 2N O

HO

O

Rx-ID: 25147414 View in Reaxys 128/361 Yield

Conditions & References 1 : Example 1 Example 1 (Preparation of Compound (1)) A mixture of anthranilic acid (0.5 g, 3.65 mmol) and 1-indanone (0.72 g, 5.45 mmol) was prepared and heated, under agitation, to 200° C. for 1.5 hours.

After cooling, the reaction mixture was rinsed with pyridine and ether to obtain a Compound (A) in the form of a crystal having a melting point of 363° to 364° C. Yield was 0.5 g (56percent).

Concentrated sulfuric acid (one drop) and phosphorus oxychloride (6 ml) was added to the compound (A) (0.40 g, 1.72 mmol) to form an admixture which was heated for 2 hours under reflux.

After completion of the reaction, the excess phosphorus oxychloride was distilled off to obtain a residue which was neutralized with concentrated aqueous ammonia, and then extracted with chloroform.

The chloroform layer was rinsed with an aqueous solution of acid potassium carbonate and water, and then the chloroform was distilled off, whereby 0.43 g (Yield: 99percent) of a Compound (2)' having a melting point of 162° to 163° C. was obtained.

The thus obtained Compound (2)' (0.20 g, 0.80 mmol) and the Compound (3) (0.18 g, 0.83 mmol) were dissolved in ethoxyethanol to form a solution which was heated for an hour under reflux.

The residue was rinsed with methanol and purified to obtain 0.24 g (Yield: 70percent) of a Compound (1) having a melting point of 245° to 250° C. Result of Ultimate Analysis (as C24 H22 N3 O3 S): Cald.: C, 61.60; H, 4.74; N, 8.98; Found: C, 61.34; H, 4.68; N, 8.75.

IRNujol cm-1: 3410, 3240, 1320.

H-NMR (DMSO-d6): δ: 3.18 (3H, S, CH3 SO2), 3.61 (2H, S, CH2), 3.78 (3H, S, CH3 O).

1

m/z: 431 (M+), 352 (M+-CH3 SO2).

Patent; Mect Corporation; US4826850; (1989); (A) English View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

H 2N

NH 2

H 2N

NH

H 2N

O

N H

N

NH 2

H 2N

HO

Rx-ID: 2109237 View in Reaxys 129/361 Yield

Conditions & References in sulfuric acid, T= 90 °C , various H2SO4 concentrations, acidity function, Kinetics, Rate constant Sycheva, E. A.; Shchel'tsyn, V. K.; Krasil'nikova, G. S.; Journal of Organic Chemistry USSR (English Translation); vol. 24; (1988); p. 184 - 189; Zhurnal Organicheskoi Khimii; vol. 24; nb. 1; (1988); p. 205 - 210 View in Reaxys Br

Br

O

O

N

OH

N

N

H

NH

N N

N NH 2 O

H N

O

H 2N O

H 2N

Br

N

NH 2

O

HO

Br

Rx-ID: 1648059 View in Reaxys 130/361 Yield

Conditions & References With hydrogenchloride, Heating, Product distribution Schleuder; Kottke; Kuhmstedt; Szkorupa; Pharmazie; vol. 42; nb. 6; (1987); p. 412 - 413 View in Reaxys Br Br

O

N

N

N

NH

N N N NH 2 O

H N

O

H 2N O

O

OH

H 2N

Br

N

NH 2

O

HO

Br

Rx-ID: 1650687 View in Reaxys 131/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With hydrogenchloride, Time= 168h, Heating, Product distribution Schleuder; Kottke; Kuhmstedt; Szkorupa; Pharmazie; vol. 42; nb. 6; (1987); p. 412 - 413 View in Reaxys

O O N H HN HN O

H

O O

HO NH 2

NH N

O

OH

H

NH 2

O

O

OH

H N

H

H 2N O

HO

HO O

H

HO

H 2N OH

Rx-ID: 3179467 View in Reaxys 132/361 Yield

Conditions & References With hydrogenchloride, Time= 24h, T= 110 °C , structure determination Kobayashi; Samejima; Nakajima; Kawai; Udagawa; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 4; (1987); p. 1347 1352 View in Reaxys

O O N H N HN O

O O NH

N H

OH

H

H

NH 2

O

OH

N H

H

H 2N

O OH

HO

HO

O

NH 2 O

HO

O

H H 2N

HO

Rx-ID: 3180014 View in Reaxys 133/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With hydrogenchloride, Time= 24h, T= 110 °C , structure determination Kobayashi; Samejima; Nakajima; Kawai; Udagawa; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 4; (1987); p. 1347 1352 View in Reaxys

O O N H N HN O

O O NH

N

OH

H

H

NH 2

O

OH

O

OH

N H

H

H N

H

H 2N O

HO

HO NH 2 O

HO

O OH

Rx-ID: 3180128 View in Reaxys 134/361 Yield

Conditions & References With hydrogenchloride, Time= 24h, T= 110 °C , structure determination Kobayashi; Samejima; Nakajima; Kawai; Udagawa; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 4; (1987); p. 1347 1352 View in Reaxys NH 2 N

H N

O

NH

H 2N O

N

H 2N

N O

HO

O

Rx-ID: 3468748 View in Reaxys 135/361 Yield

Conditions & References With hydrogenchloride, Time= 168h, Heating, Product distribution Schleuder; Kottke; Kuhmstedt; Szkorupa; Pharmazie; vol. 42; nb. 6; (1987); p. 412 - 413 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Br

NH 2 N

NH

N N

NH

O N

Br

NH 2 O

H N

O

H 2N O

H 2N

Br

N

NH 2

O

HO

Br

Rx-ID: 3823289 View in Reaxys 136/361 Yield

Conditions & References With hydrogenchloride, Time= 168h, Heating, Product distribution Schleuder; Kottke; Kuhmstedt; Szkorupa; Pharmazie; vol. 42; nb. 6; (1987); p. 412 - 413 View in Reaxys

H 2N

H 2N O

O Cl HO

OH

Rx-ID: 2732876 View in Reaxys 137/361 Yield

Conditions & References

85 %

With hydrogenchloride, dihydrogen peroxide in water, N,N-dimethyl-formamide, Time= 15h, T= 45 - 50 °C Borodina; Journal of applied chemistry of the USSR; vol. 59; nb. 5 pt 2; (1986); p. 1087 - 1089 View in Reaxys

H 2N

N O

O

O

O

N O

H 2N

HO

O

Rx-ID: 2843397 View in Reaxys 138/361 Yield 83 %

Conditions & References With sodium hydroxide, Heating Ranganathan, Darshan; Farooqui, Firdous; Bhattacharyya, Diphti; Mehrotra, Sanjiv; Kesavan, K.; Tetrahedron; vol. 42; nb. 16; (1986); p. 4481 - 4492 View in Reaxys

OH H 2N

H 2N

NH O

O

O

N

HO

H 2N

O O

NH N

N

H 2N

OH

Rx-ID: 3438406 View in Reaxys 139/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With sodium azide, sulfuric acid in 1,2-dichloro-ethane, relative proportion of anthranilazide and benzimidazol-2-one depends on reaction and isolation conditions, Product distribution Ruediger, Edward H.; Gandhi, Sham S.; Gibson, Martin S.; Farcasiu, Dan; Uncuta, Cornelia; Canadian Journal of Chemistry; vol. 64; (1986); p. 577 - 579 View in Reaxys

OH H 2N

H 2N

O

O

O

N

HO

H 2N

O N

N

H 2N

OH

Rx-ID: 3438417 View in Reaxys 140/361 Yield

Conditions & References

37 %

With sodium azide, sulfuric acid in 1,2-dichloro-ethane, Time= 1.5h, T= 35 - 45 °C Ruediger, Edward H.; Gandhi, Sham S.; Gibson, Martin S.; Farcasiu, Dan; Uncuta, Cornelia; Canadian Journal of Chemistry; vol. 64; (1986); p. 577 - 579 View in Reaxys

N O

H 2N

NH O

N

NH 2

O

HO

Rx-ID: 3817643 View in Reaxys 141/361 Yield

Conditions & References

37 %, 45 %

With sodium hydroxide, Time= 16h, Heating Ranganathan, Darshan; Farooqui, Firdous; Bhattacharyya, Diphti; Mehrotra, Sanjiv; Kesavan, K.; Tetrahedron; vol. 42; nb. 16; (1986); p. 4481 - 4492 View in Reaxys

N

H 2N O NH HO

O

Rx-ID: 20823658 View in Reaxys 142/361 Yield

Conditions & References Reaction Steps: 2 1: 40 percent / KOH / methanol / Ambient temperature 2: 45 percent / aq. NaOH / 16 h / Heating With potassium hydroxide, sodium hydroxide in methanol Ranganathan, Darshan; Farooqui, Firdous; Bhattacharyya, Diphti; Mehrotra, Sanjiv; Kesavan, K.; Tetrahedron; vol. 42; nb. 16; (1986); p. 4481 - 4492 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

O N

H 2N

O O

N O

O HO

N O OH

Rx-ID: 2095977 View in Reaxys 143/361 Yield

Conditions & References With borate buffer, water in acetone, T= 24.9 °C , ΔH (excit.), ΔS (excit.), Rate constant, Thermodynamic data Mitzner, Rolf; Seidel, Steffen; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 25; nb. 6; (1985); p. 225 - 226 View in Reaxys

O

OH

O H 2N

N O

N

O

O

O

N O

HO

Rx-ID: 3135757 View in Reaxys 144/361 Yield

Conditions & References With borate buffer, water in acetone, T= 24.9 °C , ΔH (excit.), ΔS (excit.), Rate constant, Thermodynamic data Mitzner, Rolf; Seidel, Steffen; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 25; nb. 6; (1985); p. 225 - 226 View in Reaxys

HO

O O

3H

2H

H

H 2N

2H

O

O

3H

HO

HO

O

O OH

OH

Rx-ID: 3482782 View in Reaxys 145/361 Yield

Conditions & References With L-lactate dehydrogenase, 1,4-dihydronicotinamide adenine dinucleotide, L-glutamine, anthranilate synthase, magnesium chloride, Time= 2.5h, T= 37 °C Asano, Y.; Lee, J. J.; Shieh, T. L.; Spreafico, F.; Kowal, C.; Floss, H. G.; Journal of the American Chemical Society; vol.

107; nb. 14; (1985); p. 4314 - 4320 View in Reaxys H 2N NH

N O

O

HO

Rx-ID: 1560565 View in Reaxys 146/361 Yield

Conditions & References With citrate-Pi buffer, indole 2,3-dioxygenase enzyme from Zea mays L, oxygen, Time= 0.5h, T= 40 °C , pH: 5; Km, energy of activation; effect of inhibitors on reaction rate, Equilibrium constant, Thermodynamic data

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Pundir, C. S.; Garg, G. K.; Rathore, V. S.; Phytochemistry (Elsevier); vol. 23; nb. 11; (1984); p. 2423 - 2428 View in Reaxys

O

O

OH

H 2N

N

N

N

OH O

N N

HO

HO

O

Rx-ID: 2041122 View in Reaxys 147/361 Yield

Conditions & References in toluene, Heating, Product distribution Gornostaev, L. M.; Lavrikova, T. I.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 2012 2015; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2208 - 2212 View in Reaxys OH H 2N

O O

O N

Cl HO

O

Rx-ID: 2045510 View in Reaxys 148/361 Yield

Conditions & References

100 %

With hydrogen, 10 wt. % palladium on activated carbon in methanol, Time= 80h, p= 735.5Torr Polivka; Jilek; Holubek; et al.; Collection of Czechoslovak Chemical Communications; vol. 49; nb. 1; (1984); p. 86 - 109 View in Reaxys O H 2N

NH

O

S

N H

S

HN

O

O

HO

Rx-ID: 2579224 View in Reaxys 149/361 Yield

Conditions & References With sodium hydroxide in tetrahydrofuran, Time= 0.166667h, Ambient temperature, Product distribution Davis, Michael; Hook, Robert J.; Wu, Wen Yang; Journal of Heterocyclic Chemistry; vol. 21; (1984); p. 369 - 373 View in Reaxys With hydrogenchloride in tetrahydrofuran, Time= 0.333333h, Ambient temperature, Product distribution Davis, Michael; Hook, Robert J.; Wu, Wen Yang; Journal of Heterocyclic Chemistry; vol. 21; (1984); p. 369 - 373 View in Reaxys

N H 2N

NH 2 NH

O

N N

O

HO

Rx-ID: 3127423 View in Reaxys 150/361 Yield 73 %, 79 %

Conditions & References With sodium hydroxide in water, Time= 1.5h Ranganathan, Darshan; Farooqui, Firdous; Tetrahedron Letters; vol. 25; nb. 49; (1984); p. 5701 - 5704

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys H 2N O

H 2N

HO

Rx-ID: 3377151 View in Reaxys 151/361 Yield

Conditions & References Time= 72h, T= 30 °C , Rhodococcus erythropolis AN-13, Yield given Aoki; Shinke; Nishira; Agricultural and Biological Chemistry; vol. 48; nb. 9; (1984); p. 2309 - 2313 View in Reaxys

H 2N

H 2N O

O Cl HO

OH

Rx-ID: 3569873 View in Reaxys 152/361 Yield

Conditions & References

100 %

With hydrogen, 10 wt. % palladium on activated carbon in methanol, Time= 80h, p= 735.5Torr , Ambient temperature, Product distribution Polivka; Jilek; Holubek; et al.; Collection of Czechoslovak Chemical Communications; vol. 49; nb. 1; (1984); p. 86 - 109 View in Reaxys

NH H 2N

NH 2

N

NH 2

N

N

O

HO

OH NH 2

NH 2

OH O

O NH 2 NH 2

O

HN

O

NH 2

HO

H 2N O

O HO

HO

OH

O HO

O

O

NH 2

Rx-ID: 3829956 View in Reaxys 153/361 Yield

Conditions & References

7.6 % Chro- With oxygen, ozone in water, Time= 1h, Product distribution, Mechanism mat., 0.6 % Sikorskaya; Ignatenko; Cherenkevich; Journal of applied chemistry of the USSR; vol. 57; nb. 9 pt 2; (1984); p. 1910 - 1914 Chromat., View in Reaxys 39.1 % Chromat., 7.4 % Chromat., 0.9 % Chromat., 2.7 % Chromat.

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

N

(+-)-2r-<3-bromo-2-oxo-propyl>-3t-methoxy-piperidine-1carboxylic acid ethyl ester

NH

O H 2N O

alkaline water HO

Rx-ID: 20126232 View in Reaxys 154/361 Yield

Conditions & References Reaction Steps: 2 2: 79 percent / 1 N NaOH / H2O / 1.5 h With sodium hydroxide in water Ranganathan, Darshan; Farooqui, Firdous; Tetrahedron Letters; vol. 25; nb. 49; (1984); p. 5701 - 5704 View in Reaxys

N

HO

O

O

O

O

O

H N

OH

O

OH

H N

O

N

NH

H 2N O

O

HO

O O

Rx-ID: 1719835 View in Reaxys 155/361 Yield

Conditions & References Time= 336h, Ambient temperature, other alcohols, various reagents and reaction times, Product distribution, Mechanism Errede, L.A.; Hill, J.R.; McBrady, J.J.; Journal of Organic Chemistry; vol. 47; nb. 20; (1982); p. 3829 - 3835 View in Reaxys

2

Na + H 2N

O

–O

O

S O

N H HO –O

O

Rx-ID: 2631548 View in Reaxys 156/361 Yield

Conditions & References With water, T= 50 °C , var. pH, deuterium isotope effect, Rate constant, Mechanism Hopkins, Andrew; Williams, Andrew; Journal of Organic Chemistry; vol. 47; nb. 9; (1982); p. 1745 - 1750 View in Reaxys

O

H 2N

HO O

N H

O HO

H 2N

O

Rx-ID: 2095188 View in Reaxys 157/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With hydrogenchloride, Time= 0.583333h, Yield given. Yields of byproduct given Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979 View in Reaxys

H 2N O

OH

O

O

N H HO

H 2N

O

Rx-ID: 2106160 View in Reaxys 158/361 Yield

Conditions & References With hydrogenchloride, Time= 0.583333h Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979 View in Reaxys H 2N

O H 2N O

H N

O

OH

O

HO

Rx-ID: 2177559 View in Reaxys 159/361 Yield

Conditions & References With hydrogenchloride, Time= 0.583333h Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979 View in Reaxys

O

HO

H 2N

H 2N

NH

O

O

O

HO

O

Rx-ID: 2329540 View in Reaxys 160/361 Yield

Conditions & References With dihydrogen peroxide, sodium methylate, 1.) 0-10 deg C 2.) room temperature, 30 min, Yield given. Multistep reaction Reissenweber, Gernot; Mangold, Dietrich; Angewandte Chemie; vol. 93; nb. 10; (1981); p. 914 - 915 View in Reaxys O

OH H 2N

O

H N

O

HO

Rx-ID: 3126458 View in Reaxys 161/361 Yield 8 mg

Conditions & References With hydrogenchloride, Time= 4h, Heating Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

NH 2 OH

H 2N

O

O

O

O

O

HN

O O

NH 2

HO O

O O OH

Rx-ID: 3160913 View in Reaxys 162/361 Yield

Conditions & References With sodium hydroxide, Time= 4h Arai, Kunizo; Shimizu, Sakae; Yamamoto, Yuzuru; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 1005 1012 View in Reaxys

HO

NH

NH

HO

OH NH

O

HO

melanin

O

HO

HO

O

NH 2 OH

O

O

O

H N

H 2N

HO

Rx-ID: 5737303 View in Reaxys 163/361 Yield

Conditions & References With phosphate buffer, ethylenediaminetetraacetic acid, iron(II) sulfate, ascorbic acid in water, acetone, Time= 2h, T= 37 °C , melanin formation under Udenfriend condition, oxygen atmosphere, Product distribution Roy, Shyamali; Chakraborty, A. K.; Chakraborty, D. P.; Journal of the Indian Chemical Society; vol. 58; (1981); p. 992 993 View in Reaxys

O O

H 2N O

HN

alkaline water

O HO

O

O

O

NH 2

Rx-ID: 20110810 View in Reaxys 164/361 Yield

Conditions & References Reaction Steps: 3 1: pyridine / CHCl3 / 0.5 h 2: 200 mg / 1N NaOH / 1 h / 100 °C 3: 10percent NaOH / 4 h With pyridine, sodium hydroxide in chloroform Arai, Kunizo; Shimizu, Sakae; Yamamoto, Yuzuru; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 1005 1012 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O N O H 2N

O

O O

HN

alkaline water

O HO

O O O

Rx-ID: 20111379 View in Reaxys 165/361 Yield

Conditions & References Reaction Steps: 4 1: 4.5 g / H2 / 10percent Pd/C / methanol 2: pyridine / CHCl3 / 0.5 h 3: 200 mg / 1N NaOH / 1 h / 100 °C 4: 10percent NaOH / 4 h With pyridine, sodium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in methanol, chloroform Arai, Kunizo; Shimizu, Sakae; Yamamoto, Yuzuru; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 1005 1012 View in Reaxys

O

O

O

HN

H 2N O

O

O

O

alkaline water HO

NH

O

N

Rx-ID: 20112950 View in Reaxys 166/361 Yield

Conditions & References Reaction Steps: 2 1: 200 mg / 1N NaOH / 1 h / 100 °C 2: 10percent NaOH / 4 h With sodium hydroxide Arai, Kunizo; Shimizu, Sakae; Yamamoto, Yuzuru; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 1005 1012 View in Reaxys

Cl

O

3-<δ-amino-ethyl>-indole-carboxylic acid-(2)

O N O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

alkaline water HO

Rx-ID: 20124058 View in Reaxys 167/361 Yield

Conditions & References Reaction Steps: 5 1: 82 percent / CHCl3 / 1.5 h 2: 4.5 g / H2 / 10percent Pd/C / methanol 3: pyridine / CHCl3 / 0.5 h 4: 200 mg / 1N NaOH / 1 h / 100 °C 5: 10percent NaOH / 4 h With pyridine, sodium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in methanol, chloroform Arai, Kunizo; Shimizu, Sakae; Yamamoto, Yuzuru; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 1005 1012 View in Reaxys

H 2N

H N

O

O HO

Rx-ID: 21242979 View in Reaxys 168/361 Yield

Conditions & References Reaction Steps: 2 1: 29 percent / AlCl3 / xylene / 5 h / Heating 2: conc. HCl / 0.58 h With hydrogenchloride, aluminium trichloride in xylene Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979 View in Reaxys H N

O

H 2N O

HO

Rx-ID: 21271679 View in Reaxys 169/361 Yield

Conditions & References Reaction Steps: 2 1: 40 percent / AlCl3 / xylene / 4.5 h / Heating 2: conc. HCl / 0.58 h With hydrogenchloride, aluminium trichloride in xylene Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979 View in Reaxys O OH

O

N

H 2N

O O

O

O O O O

HO

NH 2

HO

Rx-ID: 25134748 View in Reaxys 170/361 Yield 685 grams (78%)

Conditions & References F : 3,4-Dimethoxyanthranilic acid (IXa, R=CH3) PREPARATION F 3,4-Dimethoxyanthranilic acid (IXa, R=CH3)

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

A solution of 3,4-dimethoxy-2-nitro benzoic acid (1011 g., 4.45 moles) in 14 liters of 1.3 N ammonium hydroxide was reduced at 60 psi in presence of 60 grams of palladium on barium carbonate.

Hydrogen uptake ceased after four hours.

The reaction mixture was filtered through diatomaceous earth and acidified with glacial acetic acid (1.2 liters) to yield 685 grams (78percent) of the anthranilic acid, M.P. 183°-184° C. in ammonium hydroxide Patent; Pfizer Inc.; US4287341; (1981); (A) English View in Reaxys H 2N

O

O

O

S

NH 2

HO

HO

Rx-ID: 25283273 View in Reaxys 171/361 Yield

Conditions & References 92 : EXAMPLE 92 EXAMPLE 92 7 parts of malodinitrile and 55 parts of the azomethine of the formula STR110 prepared analogously to Example 17 of U.S. Pat. No. 2,583,551 from N-δ-(4-tert.-butylphenoxy)-ethyl-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline, are heated to the boil for about 3 hours in 800 parts by volume of methanol in the presence of 3 parts of piperidine.

The dyestuff which has separated out is isolated and purified in the usual manner and about 32.5 parts of the dyestuff of the formula STR111 are obtained.

This can be purified further by recrystallisation from ethanol (melting point 124° - 125° C).

It has a high stability to boiling in the dye bath and dyes polyester fibres in brilliant greenish-tinged yellow shades with good fastness to light, wet processing and sublimation.

The same dyestuff is obtained by starting from other azomethines, for example from those which in place of metanilic acid are derived from sulphanilic acid, anthranilic acid or aniline and can be prepared, and converted to the styryl dyestuff, in an analogous manner.

Patent; Bayer Aktiengesellschaft; US4077962; (1978); (A) English View in Reaxys

H 2N

N O

O

HO

HO NH 2 O

Rx-ID: 25212161 View in Reaxys 172/361 Yield

Conditions & References 35.E.b : Method E b.

3-(1-Pyrrolidinyl)-4-phenoxy-5-aminobenzoic acid.

32.8 g of the nitrobenzoic acid prepared according to (a) are dissolved in a solution of 8 g of NaOH in 200 ml of water, cooled to 0° C and combined with a solution of 90 g of sodium dithionite in 380 ml of water, while keeping the temperature below 10° C. The solution which at first is red-orange coloured changes to light yellow.

The solution is stirred for 1 hour without cooling, then acidified to pH 1 by means of concentrated hydrochloric acid and concentrated until crystallisation begins.

The hydrochloride of the desired aminobenzoic acid is obtained in the form of colourless crystals melting at 245°-247° C. If the dithionite contains sulfate, there is obtained already before concentration of the aqueous solution the corresponding sulphate in the form of colourless crystals melting at 175°-176° C. From both, the free amine melting at 100°-103° C can be obtained by neutralisation of the aqueous solution to pH 4-4.5.

Patent; Hoechst Aktiengesellschaft; US4010273; (1977); (A) English

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys

NH

NH

H

H 2N O

O O

H

O

HO OH

O

Rx-ID: 5673683 View in Reaxys 173/361 Yield

Conditions & References Gray; Archives of Biochemistry; vol. 81; (1959); p. 480,483 View in Reaxys

NH O

aqueous potassium permanganate solution

O

NH

H 2N O O

HO OH

Rx-ID: 5673684 View in Reaxys 174/361 Yield

Conditions & References Gray; Archives of Biochemistry; vol. 81; (1959); p. 480,483 View in Reaxys

NH

OH

H

H O

H 2N O

<3,2';2',3''>terindol-3'one HO

Rx-ID: 5723487 View in Reaxys 175/361 Yield

Conditions & References mit Sonnenlicht.Irradiation Sakamura; Obata; Bulletin of the Agricultural Chemical Society of Japan; vol. 20; (1956); p. 80,81 View in Reaxys

NH

H

H

NH 2

O

KO H

K2S2O8

OH O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

OH

O

kynurenin H

HO

Rx-ID: 5736395 View in Reaxys 176/361 Yield

Conditions & References Boyland et al.; Biochemical Journal; vol. 62; (1956); p. 546,548 View in Reaxys O

N

Cl

H 2N

Cl

O

N

Cl

Cl HO

O

Rx-ID: 594842 View in Reaxys 177/361 Yield

Conditions & References T= 320 °C de Diesbach; Lempen; Helvetica Chimica Acta; vol. 16; (1933); p. 148,151 View in Reaxys de Diesbach; Moser; Helvetica Chimica Acta; vol. 20; (1937); p. 132,138 View in Reaxys Staunton; Topham; Journal of the Chemical Society; (1953); p. 1889,1891 View in Reaxys de Diesbach et al.; Helvetica Chimica Acta; vol. 17; (1934); p. 113,122; Helvetica Chimica Acta; vol. 23; (1940); p. 469,481 View in Reaxys H N

O

H N

O

K2CO3

O

H N

O

H 2N

O O

N

NH 2 HO

O

HO

Rx-ID: 5820556 View in Reaxys 178/361 Yield

Conditions & References T= 250 - 255 °C , p= 55 - 36775.4Torr Kisber; Glagolewa; Zhurnal Obshchei Khimii; vol. 23; (1953); p. 1028,1030; engl. Ausg. S. 1077, 1079 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O O N

OH

alkalimelt N

O

N H 2N O O

HO

O HO

O

Rx-ID: 5690852 View in Reaxys 179/361 Yield

Conditions & References T= 245 - 255 °C De Diesbach et al.; Helvetica Chimica Acta; vol. 34; (1951); p. 1050,1059 View in Reaxys de Diesbach et al.; Helvetica Chimica Acta; vol. 17; (1934); p. 113,122; Helvetica Chimica Acta; vol. 23; (1940); p. 469,481 View in Reaxys H 2N

H 2N O

Li

Br

HO

Rx-ID: 779893 View in Reaxys 180/361 Yield

Conditions & References With diethyl ether, Behandeln des Reaktionsgemisches mit festem Kohlendioxid Gilman; Stuckwisch; Journal of the American Chemical Society; vol. 71; (1949); p. 2933 View in Reaxys O

H 2N O

O

HO

HO

sodium hydroxide

N

O

Rx-ID: 5673679 View in Reaxys 181/361 Yield

Conditions & References T= 280 °C de Diesbach; Schuerch; Cavin; Helvetica Chimica Acta; vol. 31; (1948); p. 716,719 View in Reaxys O H 2N O

N

Br

HO

O

Rx-ID: 121804 View in Reaxys 182/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References With potassium hydroxide Putochin; Zhurnal Obshchei Khimii; vol. 15; (1945); p. 332,337; ; (1946); p. 3741 View in Reaxys

NH

KO H

O O O

O

H 2N O

2-<1-methoxy-ethyl>-3-isobutyl-cinchoninic acid HO

Rx-ID: 7056628 View in Reaxys 183/361 Yield

Conditions & References T= 115 - 120 °C Isbell; Henze; Journal of the American Chemical Society; vol. 66; (1944); p. 2096 View in Reaxys

H

O

O H

O H

N OH Cl

H

H

H

H

O

O

O

OH

O

O N

O

H

H 2N

O O

HO

lycoctonine OH HO

O

Rx-ID: 5737219 View in Reaxys 184/361 Yield

Conditions & References Goodson; Journal of the Chemical Society; (1943); p. 139,140; Journal of the Chemical Society; (1944); p. 665 View in Reaxys

H N

H 2N

NH

H H

H O

H

O O

O

O

H

H

O

HO

Rx-ID: 5673657 View in Reaxys 185/361 Yield

Conditions & References Jacini; Gazzetta Chimica Italiana; vol. 72; (1942); p. 510,514 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

H N

OH

O

H 2N

H N

O

O NH 2

O

O

HO

Rx-ID: 133606 View in Reaxys 186/361 Yield

Conditions & References With water Caronna; Gazzetta Chimica Italiana; vol. 71; (1941); p. 189,192 View in Reaxys O OH

O HO

sodium azide

S OO

O

H N

O

H 2N

NH

O

O

O

NH

HO

O

Rx-ID: 5673682 View in Reaxys 187/361 Yield

Conditions & References Caronna; Gazzetta Chimica Italiana; vol. 71; (1941); p. 189,192 View in Reaxys H 2N O

sodium-salt of 2-nitro-benzoic acid HO

Rx-ID: 5820555 View in Reaxys 188/361 Yield

Conditions & References With dihydrogen hexachloroplatinate, ethanol, nickel, Hydrogenation Scholnik et al.; Journal of the American Chemical Society; vol. 63; (1941); p. 1192 View in Reaxys H 2N O

H 2N

Li

HO

Rx-ID: 706476 View in Reaxys 189/361 Yield

Conditions & References anschl. mit CO2 Gilman et al.; Journal of the American Chemical Society; vol. 62; (1940); p. 977 View in Reaxys

O N

concentrated aqueous KOH

O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N

O

O –C

N

N

N

H 2N

HO

Rx-ID: 7448354 View in Reaxys 190/361 Yield

Conditions & References T= 200 °C Lock; Chemische Berichte; vol. 73; (1940); p. 1377,1381 View in Reaxys

OH H 2N

O

O

OH

O

HO

S OO

N

HO

O

Rx-ID: 7443795 View in Reaxys 191/361 Yield

Conditions & References T= 80 °C , Reduktion an Blei-Kathoden Shipley; Calhoun; Canadian Journal of Research, Section B: Chemical Sciences; vol. 13; (1935); p. 123,125, 131 View in Reaxys

NH

O

O

N H

H

H O

O

O

O

O

H

OH

O

HO

O H 2N O

NH 2

OH

HO

Rx-ID: 5673691 View in Reaxys 192/361 Yield

Conditions & References Inagaki; Yakugaku Zasshi; vol. 53; (1933); p. 686,696;dtsch.Ref.S.133; Chem. Zentralbl.; vol. 104; nb. II; (1933); p. 2133 View in Reaxys O H 2N O

3.3-bis-<4-hydroxy-phenyl>-indolinone-(2) NH 2

OH

HO

Rx-ID: 7917287 View in Reaxys 193/361 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide Inagaki; Yakugaku Zasshi; vol. 53; (1933); p. 686,696;dtsch.Ref.S.133; Chem. Zentralbl.; vol. 104; nb. II; (1933); p. 2133 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH H 2N

O

O

O HO

OH

Rx-ID: 735309 View in Reaxys 194/361 Yield

Conditions & References With sodium azide, chloroform, sulfuric acid, T= 50 °C Oesterlin; Angewandte Chemie; vol. 45; (1932); p. 536 View in Reaxys OH H 2N

Cl

Cl HO

Cl

OH

O

S OO

O

H 2N

O

sodium azide H 2N

HO

OH

Rx-ID: 5930856 View in Reaxys 195/361 Yield

Conditions & References T= 45 - 50 °C Oesterlin; Angewandte Chemie; vol. 45; (1932); p. 536 View in Reaxys

OH H 2N

O

O

O

O

O

OH

O

tin (II)-chloride

O N

HO

O

Rx-ID: 7443809 View in Reaxys 196/361 Yield

Conditions & References de Kiewiet; Stephen; Journal of the Chemical Society; (1931); p. 82 View in Reaxys

H 2N

O

HO S

O–

O

Na +

H 2N

O O

N O

O

OH

OH

S O

HO

OH

O

Rx-ID: 26471937 View in Reaxys 197/361 Yield 65 %, 21 %

Conditions & References 4.5 h boiling Hunter, W. H.; Sprung, M. M.; Journal of the American Chemical Society; vol. 53; (1931); p. 1432 - 1443 ; (from Gmelin) View in Reaxys

65 %, 21 %

4.5 h boiling vol. S: MVol.B2; 3.1.2, page 596 - 602 ; (from Gmelin) View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH H 2N

O

Cl

O

H

tin (II)-chloride

O N

HO

O

Rx-ID: 7443808 View in Reaxys 198/361 Yield

Conditions & References T= 75 °C , Kinetics Sampey; Journal of the American Chemical Society; vol. 52; (1930); p. 88 View in Reaxys

O O

HN

HN

NH

diluted NaOH-solution

O

H 2N O O

4-<2-carboxy-phenyl>-3.5-diphenyl-1.2.4-triazole HO HO

Rx-ID: 7919297 View in Reaxys 199/361 Yield

Conditions & References Heller; Journal fuer Praktische Chemie (Leipzig); vol. <2> 120; (1929); p. 63 View in Reaxys O H 2N O

N

OH

aqueous-isopentyl alcoholic KOH-solution HO

O

Rx-ID: 5673663 View in Reaxys 200/361 Yield

Conditions & References Brady et al.; Journal of the Chemical Society; (1928); p. 533 View in Reaxys O H 2N O

OH

N

OH

potassium hydroxide HO

O

Rx-ID: 5673668 View in Reaxys 201/361 Yield

Conditions & References Lassar-Cohn; Justus Liebigs Annalen der Chemie; vol. 205; (1880); p. 295 View in Reaxys Patent; Basler Chem.Fabr.; DE130302; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 152 View in Reaxys Brady et al.; Journal of the Chemical Society; (1928); p. 533 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Cl

H

H

H 2N

O

N

O

chromium powder H HO

HO

Rx-ID: 5820549 View in Reaxys 202/361 Yield

Conditions & References Chakrabarty; Dutt; Journal of the Indian Chemical Society; vol. 5; (1928); p. 514; Chem. Zentralbl.; vol. 100; nb. I; (1929); p.

501 View in Reaxys H 2N O

N,N-phthalyl-hydroxylamine HO

Rx-ID: 5820551 View in Reaxys 203/361 Yield

Conditions & References Brady et al.; Journal of the Chemical Society; (1928); p. 533 View in Reaxys OH

H 2N

N

O

O

OH

N HO

Rx-ID: 154357 View in Reaxys 204/361 Yield

Conditions & References bei der Kalischmelze Ghose; Journal of the Indian Chemical Society; vol. 4; (1927); p. 3; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 439 View in Reaxys H 2N

H 2N

O

O

HO

HO

Rx-ID: 457178 View in Reaxys 205/361 Yield

Conditions & References Mazza; Crapetta; Gazzetta Chimica Italiana; vol. 57; (1927); p. 293,295 View in Reaxys O O

H 2N

N

O

zinc dust

N

alkaline solution

O

HO

O

Rx-ID: 5673675 View in Reaxys 206/361 Yield

Conditions & References Arndt; Partale; Chemische Berichte; vol. 60; (1927); p. 451 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH H 2N

O

OH

O

platinum oxide

O N

HO

O

Rx-ID: 7443802 View in Reaxys 207/361 Yield

Conditions & References T= 25 - 30 °C , p= 1900 - 2280Torr , Hydrogenation Adams; Cohen; Rees; Journal of the American Chemical Society; vol. 49; (1927); p. 1095 View in Reaxys O

OH H 2N

H N

O

N

OH

H 2N

O

zinc

N

Br

Br

Br

Br

HO

Rx-ID: 8252025 View in Reaxys 208/361 Yield

Conditions & References Chattaway; Walker; Journal of the Chemical Society; (1927); p. 329 View in Reaxys O

OH H 2N

H N

O

N

OH

H 2N

O

zinc

N

Cl

Cl

Cl

Cl

HO

Rx-ID: 8252028 View in Reaxys 209/361 Yield

Conditions & References Chattaway; Walker; Journal of the Chemical Society; (1927); p. 329 View in Reaxys O

NH 2

H N

Cl

Br

HN

O

N H

H

H 2N

H 2N

HO

Br

Br

Br

Rx-ID: 8262086 View in Reaxys 210/361 Yield

Conditions & References T= 100 °C , im Rohr Chattaway; Walker; Journal of the Chemical Society; (1927); p. 329 View in Reaxys O N

O O

aluminium amalgam

O

N N

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N

NH O

N

HO

Rx-ID: 5673680 View in Reaxys 211/361 Yield

Conditions & References v. Auwers; Allardt; Chemische Berichte; vol. 59; (1926); p. 98 View in Reaxys O N

O O

OH

aluminium amalgam N N

H 2N

NH O

N

HO

Rx-ID: 5673681 View in Reaxys 212/361 Yield

Conditions & References v. Auwers; Allardt; Chemische Berichte; vol. 59; (1926); p. 98 View in Reaxys H 2N

O

O

O

6-bromo-benzoic acid sulfonic acid-(3)

S

NH 2

HO

HO

Rx-ID: 6190349 View in Reaxys 213/361 Yield

Conditions & References With ammonia, T= 180 °C van Dorssen; Recueil des Travaux Chimiques des Pays-Bas; vol. 29; (1910); p. 383 View in Reaxys Keller; Schulze; Archiv der Pharmazie (Weinheim, Germany); (1925); p. 494 View in Reaxys O H 2N

H 2N

O

sodium hypochlorite

O

HO

OH

Rx-ID: 7056627 View in Reaxys 214/361 Yield

Conditions & References Zufuegen von Natronlauge und Erwaermen auf 80grad Chapman; Stephen; Journal of the Chemical Society; vol. 127; (1925); p. 1794 View in Reaxys Hoogewerff; van Dorp; Recueil des Travaux Chimiques des Pays-Bas; vol. 10; (1891); p. 6 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

HO

H 2N

NH 2

H N

OH

O

N H

S OO

O

HO

Rx-ID: 7443796 View in Reaxys 215/361 Yield

Conditions & References Heller; Journal fuer Praktische Chemie (Leipzig); vol. <2> 111; (1925); p. 48 View in Reaxys N H 2N

N H

O

H O

O

HO

O

Rx-ID: 5673656 View in Reaxys 216/361 Yield

Conditions & References Karrer; Diechmann; Haebler; Helvetica Chimica Acta; vol. 7; (1924); p. 1036 View in Reaxys

H 2N

H 2N

N

O

potash S

HO

Rx-ID: 5673667 View in Reaxys 217/361 Yield

Conditions & References bei der Schmelze Levi; ; (1924); p. 400; Chem. Zentralbl.; vol. 96; nb. I; (1925); p. 2307 View in Reaxys

O

O

O N

S

O

N O O

NH

O

H 2N O

naphthsultam-aldehyde-(2) HO

Rx-ID: 5739399 View in Reaxys 218/361 Yield

Conditions & References Koenig; Wagner; Chemische Berichte; vol. 57; (1924); p. 1059 View in Reaxys H 2N N

H 2N O

Cl

H

OH

O

3-phenyl-2-methyl-quinazolone-(4)

HN

HO

Rx-ID: 7917288 View in Reaxys 219/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References Shah; Journal of the Indian Institute of Science; vol. 7; (1924); p. 217; Chem. Zentralbl.; vol. 96; nb. I; (1925); p. 659 View in Reaxys

HO

O

O H 2N

HN

H

H O

N

O

O H

N H

HO

O

OH

Rx-ID: 7920245 View in Reaxys 220/361 Yield

Conditions & References T= 110 °C , im Rohr Bogert; Nabenhauer; Journal of the American Chemical Society; vol. 46; (1924); p. 1705,1933 View in Reaxys

NH

OH H 2N O

O

rutaecarpin

HO

NH 2

Rx-ID: 5673688 View in Reaxys 221/361 Yield

Conditions & References With potassium hydroxide, i-Amyl alcohol Asahina; Acta Phytochimica; vol. 1; (1922); p. 81; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 248 View in Reaxys Asahina; Fujita; Yakugaku Zasshi; nb. 476; (1921) View in Reaxys With potassium hydroxide, i-Amyl alcohol Asahina; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 250 View in Reaxys

O N N H

isopentyl alcoholic KOH-solution N

H 2N O

3-<δ-amino-ethyl>-indole-carboxylic acid-(2) HO

Rx-ID: 5673694 View in Reaxys 222/361 Yield

Conditions & References Asahina; Acta Phytochimica; vol. 1; (1922); p. 81; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 248 View in Reaxys Asahina; Fujita; Yakugaku Zasshi; (1921); p. 476,1; ; vol. 16; (1922); p. 1584; Chem. Zentralbl.; vol. 93; nb. I; (1922); p. 357 View in Reaxys Asahina; Mayeda; Yakugaku Zasshi; (1916); p. 416; ; vol. 11; (1917); p. 332 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

NH O

OH

HN

O

H 2N

H N

O

HN

N

H 2N

NH HO

Rx-ID: 722689 View in Reaxys 223/361 Yield

Conditions & References Scholtz; Chemische Berichte; vol. 51; (1918); p. 1649 View in Reaxys

O O

OH

O H 2N

O

O

Cl

H

O

O

O O HO

N

OH

O

Rx-ID: 5688443 View in Reaxys 224/361 Yield

Conditions & References Gabriel; Loewenberg; Chemische Berichte; vol. 51; (1918); p. 1496 View in Reaxys

O O

OH

O H 2N

O

O

O

O

O

Br

H O HO

N

OH

O

Rx-ID: 5688444 View in Reaxys 225/361 Yield

Conditions & References Gabriel; Loewenberg; Chemische Berichte; vol. 51; (1918); p. 1496 View in Reaxys

H 2N NH

O

O

N H

HO

O

OH

Rx-ID: 51418 View in Reaxys 226/361 Yield

Conditions & References With water, oxygen, Licht Baudisch; Hoschek; Chemische Berichte; vol. 49; (1916); p. 2580 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

NH

H

H

oxygen

O

H 2N O

O

bis-<2-methyl-indolyl-(3)>-ether

N H

HO

O

OH

Rx-ID: 5726469 View in Reaxys 227/361 Yield

Conditions & References Irradiation Baudisch; Hoschek; Chemische Berichte; vol. 49; (1916); p. 2580 View in Reaxys Oddo; Gazzetta Chimica Italiana; vol. 46 I; (1916); p. 325 View in Reaxys O

O N

H 2N

NH

N O

O

O

O

N

O

O

O

HO

Rx-ID: 322597 View in Reaxys 228/361 Yield

Conditions & References Perkin; Proceedings of the Chemical Society, London; vol. 22; (1906); p. 198; Chem. News J. Ind. Sci.; vol. 94; (1906); p. 44 View in Reaxys Friedlaender; Roschdestwensky; Chemische Berichte; vol. 48; (1915); p. 1843 View in Reaxys

O NH

H 2N NH

O

HN

HO

OH

O

O

Rx-ID: 118704 View in Reaxys 229/361 Yield

Conditions & References With sodium hydroxide, ozone, acetone Patent; Ges. f. Teerverwertung; DE230542; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 356 View in Reaxys Weissgerber; Chemische Berichte; vol. 46; (1913); p. 654 View in Reaxys

NH

O (v4)

O

O

diluted NaOH-solution

O

OH O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

H 2N NH

O

HN

HO O

Rx-ID: 5712157 View in Reaxys 230/361 Yield

Conditions & References Patent; Ges. f. Teerverwertung; DE230542; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 356 View in Reaxys Weissgerber; Chemische Berichte; vol. 46; (1913); p. 654 View in Reaxys O O OH

N

H

O

H

KOH-solution

O

O O

OH

O

H 2N

HO

O

N H HO

Rx-ID: 5673690 View in Reaxys 231/361 Yield

Conditions & References Orndorff; Pratt; American Chemical Journal; vol. 47; (1912); p. 113 View in Reaxys

Cl

H

H 2N

O

O

O

HO

HO

OH

N H O

O O

HO

OH

Rx-ID: 7443812 View in Reaxys 232/361 Yield

Conditions & References Riedel,J. D.; Chem. Zentralbl.; vol. 83; nb. I; (1912); p. 1774 View in Reaxys OH

O

O H 2N

O HN

Cl

OH

H

O

O

HO O

HO

OH HO

O

Rx-ID: 8252027 View in Reaxys 233/361 Yield

Conditions & References Riedel,J. D.; Chem. Zentralbl.; vol. 83; nb. I; (1912); p. 1774 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

O

H 2N

H 2N

O

O–

OH K+

O

O

O

HO

HO

O

OH O

Rx-ID: 37306603 View in Reaxys 234/361 Yield

Conditions & References Reaction Steps: 2 1: water With water Riedel,J. D.; Chem. Zentralbl.; vol. 83; nb. I; (1912); p. 1774 View in Reaxys O

H 2N

O

NH

NH

O

HN

HO

OH

O

Rx-ID: 820466 View in Reaxys 235/361 Yield

Conditions & References With potassium hydroxide, T= 150 °C Friedlaender; Kielbasinski; Chemische Berichte; vol. 44; (1911); p. 3107 View in Reaxys Friedlaender; Schwenk; Chemische Berichte; vol. 43; (1910); p. 1973 View in Reaxys

S O

NH O

alkaline solution

H 2N O

2-oxy-3-formyl-thionaphthene HO

Rx-ID: 5673692 View in Reaxys 236/361 Yield

Conditions & References Friedlaender; Kielbasinski; Chemische Berichte; vol. 44; (1911); p. 3107 View in Reaxys Friedlaender; Chemische Berichte; vol. 41; (1908); p. 1038 View in Reaxys Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 29; (1908); p. 383; Monatshefte fuer Chemie; vol. 30; (1909); p. 278 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

NH O

OH O

KOH-solution

NH O

OH

H 2N

HO

NH

OH

O

O

H 2N 2 O HO

OH

Rx-ID: 5706778 View in Reaxys 237/361 Yield

Conditions & References T= 85 °C Kalb; Chemische Berichte; vol. 44; (1911); p. 1455,1456; Chemische Berichte; vol. 42; (1909); p. 3643 View in Reaxys O

NH

O

O

diluted NaOH-solution N H

O O

O O

H 2N

NH

NH

O

O

diisatinic acid HN

HO

O

O

Rx-ID: 5732387 View in Reaxys 238/361 Yield

Conditions & References Product distribution Kalb; Chemische Berichte; vol. 44; (1911); p. 1455,1456; Chemische Berichte; vol. 42; (1909); p. 3643 View in Reaxys OH O

OH

Cl

H

NH

H

N

H O

OH H 2N O

OH

O

indoxyl-aldehyde-(2)-indogenide H

HO

Rx-ID: 5735559 View in Reaxys 239/361 Yield

Conditions & References Friedlaender; Kielbasinski; Chemische Berichte; vol. 44; (1911); p. 3107

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys O

O

O

O

H 2N

N

O O

O O HN

HO

O

O

O

Rx-ID: 355448 View in Reaxys 240/361 Yield

Conditions & References Felix; Friedlaender; Monatshefte fuer Chemie; vol. 31; (1910); p. 59 View in Reaxys

H 2N

-2

NH

H

(v1)

H

O

O

N

O

Fe 2+ S

H (v1)

O

O

O O

HO

Rx-ID: 5673658 View in Reaxys 241/361 Yield

Conditions & References Heller; Chemische Berichte; vol. 43; (1910); p. 1915 View in Reaxys

H 2N

NH

O

OH

O

O

tin HO

O

Rx-ID: 5673673 View in Reaxys 242/361 Yield

Conditions & References Heller; Chemische Berichte; vol. 43; (1910); p. 1915 View in Reaxys

H 2N

NH

O

OH

O

O

zinc dust HO

O

Rx-ID: 5673674 View in Reaxys 243/361 Yield

Conditions & References Heller; Chemische Berichte; vol. 43; (1910); p. 1915 View in Reaxys

O O

O

N O O

N

NH

N

O

H 2N O

1-phenyl-3-methyl-pyrazolon-(5)-aldehyde-(4) HO

Rx-ID: 5673687 View in Reaxys 244/361 Yield

Conditions & References Felix; Friedlaender; Monatshefte fuer Chemie; vol. 31; (1910); p. 59

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys O NH

KOH-solution HN O

H 2N O

indoxylaldehyde-(2) HO

Rx-ID: 5735560 View in Reaxys 245/361 Yield

Conditions & References T= 150 °C Hentschel; Journal fuer Praktische Chemie (Leipzig); vol. <2> 60; (1899); p. 577 View in Reaxys Boettinger; Chemische Berichte; vol. 10; (1877); p. 269 View in Reaxys Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys Liebig; Justus Liebigs Annalen der Chemie; vol. 39; (1841); p. 91 View in Reaxys Fritzsche; Journal fuer Praktische Chemie (Leipzig); vol. <1> 23; (1841); p. 67; Justus Liebigs Annalen der Chemie; vol. 39; (1841); p. 76,83 View in Reaxys Friedlaender; Schwenk; Chemische Berichte; vol. 43; (1910); p. 1973 View in Reaxys H 2N O

benzisoxazolone HO

Rx-ID: 5820548 View in Reaxys 246/361 Yield

Conditions & References With acetic acid, zinc Heller; Chemische Berichte; vol. 43; (1910); p. 1915 View in Reaxys With tin, acetic acid Heller; Chemische Berichte; vol. 43; (1910); p. 1915 View in Reaxys With ammonia, iron(II) sulfate Heller; Chemische Berichte; vol. 43; (1910); p. 1915 View in Reaxys O O

O N

N O

OH

O

O

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O

zinc dust O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

aldehyde C14H12ON2 or C14H14ON2

o-azobenzaldehyde bis-dimethylacetal HO

<3-oxy-indazyl-(2)>-benzoic acid-lactone Rx-ID: 7456359 View in Reaxys 247/361 Yield

Conditions & References Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 143; (1906); p. 54; Bulletin de la Societe Chimique de France; vol. <3> 35; (1906); p. 1276 View in Reaxys Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 289; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 450 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8>19; (1910); p. 220; Bulletin de la Societe Chimique de France; vol. <4>5; (1909); p. 121 View in Reaxys OH

O N

N

O

OH

O

O

O

zinc dust

N

O

O

H 2N O

o-indazyl-benzyl alcohol

o-indazyl-benzoic acid

HO

Rx-ID: 7456462 View in Reaxys 248/361 Yield

Conditions & References Product distribution Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 143; (1906); p. 54; Bulletin de la Societe Chimique de France; vol. <3> 35; (1906); p. 1276 View in Reaxys Freundler; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 882 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8>19; (1910); p. 220; Bulletin de la Societe Chimique de France; vol. <4>5; (1909); p. 121 View in Reaxys Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 371;138,1425; Bulletin de la Societe Chimique de France; vol. <3>31; (1904); p. 880 View in Reaxys OH

OH H 2N

O

H

S O

O

H N

O

O

S

O H

Br

NH 2

HO

HO

Rx-ID: 8264401 View in Reaxys 249/361 Yield

Conditions & References T= 180 °C van Dorssen; Recueil des Travaux Chimiques des Pays-Bas; vol. 29; (1910); p. 383 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N

NH O

O

HO

O

Rx-ID: 89920 View in Reaxys 250/361 Yield

Conditions & References With sulfuric acid, zinc Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys

H 2N

NH O

O

aluminium amalgam HO

O

Rx-ID: 5673661 View in Reaxys 251/361 Yield

Conditions & References Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys

H 2N

NH O

O

ammonium sulfide HO

O

Rx-ID: 5673662 View in Reaxys 252/361 Yield

Conditions & References Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys O H 2N

HN O

KOH-solution N H

HO

O

Rx-ID: 5673666 View in Reaxys 253/361 Yield

Conditions & References Schroeter; Eisleb; Justus Liebigs Annalen der Chemie; vol. 367; (1909); p. 158 View in Reaxys

H 2N

NH O

O

sodium amalgam

O

HO

Rx-ID: 5673670 View in Reaxys 254/361 Yield

Conditions & References Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N

NH O

OH

O HO

zinc

S OO

HO

O

Rx-ID: 5673676 View in Reaxys 255/361 Yield

Conditions & References Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys O H 2N

N

NH

O

O

O

O

zinc HO

O

O

Rx-ID: 5673677 View in Reaxys 256/361 Yield

Conditions & References Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys

O

O

O

N O O

NH

O OH H 2N O

1.5-dioxy-naphthaldehyde-(2) HO

Rx-ID: 5673678 View in Reaxys 257/361 Yield

Conditions & References Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 30; (1909); p. 280 View in Reaxys O Cl

O H 2N

N O

O O

3-chloro-4-oxy-naphthaldehyde-(1)

O HN HO

O

Rx-ID: 5673695 View in Reaxys 258/361 Yield

Conditions & References Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 30; (1909); p. 280 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H N

O

natrium carbonate

O

O

H 2N

O

HO

OH

O

N H

H 2N 2

N H

O HO

HO

O

O

OH

Rx-ID: 5684128 View in Reaxys 259/361 Yield

Conditions & References Mohr; Journal fuer Praktische Chemie (Leipzig); vol. <2> 79; (1909); p. 324 View in Reaxys Erdmann; Chemische Berichte; vol. 32; (1899); p. 2164; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 506 View in Reaxys

O N

O

O O O NH

O

H 2N O

anthrol-(2)-aldehyde-(1) HO

Rx-ID: 5725600 View in Reaxys 260/361 Yield

Conditions & References Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 30; (1909); p. 875 View in Reaxys

H 2N O

OH HO

O

S

S OO

N H

O

O O

S

HO

HO HO

O

Rx-ID: 7919836 View in Reaxys 261/361 Yield

Conditions & References Schroeter; Eisleb; Justus Liebigs Annalen der Chemie; vol. 367; (1909); p. 158 View in Reaxys OH HN

O

absolute alcoholic KOH-solution

HO

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH

O H 2N

O

OH

O

O

N N

O N

HO

HO

O

O

Rx-ID: 7920534 View in Reaxys 262/361 Yield

Conditions & References T= 20 °C Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys OH H 2N HN O

O

HO HO

Rx-ID: 22002109 View in Reaxys 263/361 Yield

Conditions & References Reaction Steps: 2 1: sulfuric acid 2: zinc dust; diluted sulfuric acid With sulfuric acid, zinc Bamberger; Pyman; Chemische Berichte; vol. 42; (1909); p. 2312; Chemische Berichte; vol. 36; (1903); p. 2700 View in Reaxys

O H 2N

N

O

O

O O O

HO

NH HO

O

O

Rx-ID: 345715 View in Reaxys 264/361 Yield

Conditions & References Friedlaender; Chemische Berichte; vol. 41; (1908); p. 1038 View in Reaxys Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 28; (1907); p. 381 View in Reaxys Patent; Kalle and Co.; DE209910; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 9; p. 159 View in Reaxys

O

HN

O N O O O

O O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

1-oxy-4-methoxy-naphthaldehyde-(2) HO

Rx-ID: 5673685 View in Reaxys 265/361 Yield

Conditions & References Friedlaender; Chemische Berichte; vol. 41; (1908); p. 1038 View in Reaxys Patent; Kalle and Co.; DE209910; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 9; p. 159 View in Reaxys Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 29; (1908); p. 383; Monatshefte fuer Chemie; vol. 30; (1909); p. 278 View in Reaxys

O O

HN

N O O

O

O

H 2N O

1-oxy-naphthaldehyde-(2) HO

Rx-ID: 5673686 View in Reaxys 266/361 Yield

Conditions & References Friedlaender; Chemische Berichte; vol. 41; (1908); p. 1038 View in Reaxys Patent; Kalle and Co.; DE209910; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 9; p. 159 View in Reaxys Bezdzik; Friedlaender; Monatshefte fuer Chemie; vol. 29; (1908); p. 383; Monatshefte fuer Chemie; vol. 30; (1909); p. 278 View in Reaxys O H 2N N O

O

HO HO

Rx-ID: 281728 View in Reaxys 267/361 Yield

Conditions & References With hydrogenchloride, tin(ll) chloride Heller; Chemische Berichte; vol. 39; (1906); p. 2345 View in Reaxys With ammonium sulfide, T= 100 °C Fischer,E.; Chemische Berichte; vol. 29; (1896); p. 2063 View in Reaxys With sodium sulfide Heller; Chemische Berichte; vol. 39; (1906); p. 2345 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O H 2N N O O

sodium sulfide HO

HO

Rx-ID: 7443806 View in Reaxys 268/361 Yield

Conditions & References Heller; Chemische Berichte; vol. 39; (1906); p. 2345 View in Reaxys O H 2N N O

Cl

H

O

tin dichloride HO

HO

Rx-ID: 7443807 View in Reaxys 269/361 Yield

Conditions & References Heller; Chemische Berichte; vol. 39; (1906); p. 2345 View in Reaxys O OH

O N

H 2N O

N HO

Rx-ID: 22295010 View in Reaxys 270/361 Yield

Conditions & References Reaction Steps: 2 1: alcoholic ammonia 2: sodium sulfide With sodium sulfide, ammonia Heller; Chemische Berichte; vol. 39; (1906); p. 2345 View in Reaxys OH

Oâ&#x20AC;&#x201C; O

Na +

N O

H 2N

H 2N

H 2N

N O

O

HO

HO

O

Rx-ID: 308173 View in Reaxys 271/361 Yield

Conditions & References Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 664; Bulletin de la Societe Chimique de France; vol. <3> 33; (1905); p. 1165 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8> 6; (1905); p. 412; Annales de Chimie (Cachan, France); vol. <8> 19; (1910); p. 210 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH

O

alcoholic NaOH-solution N

O

H 2N

H 2N

H 2N

N O

O

HO

HO

O

Rx-ID: 7445113 View in Reaxys 272/361 Yield

Conditions & References Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 664; Bulletin de la Societe Chimique de France; vol. <3> 33; (1905); p. 1165 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8> 6; (1905); p. 412; Annales de Chimie (Cachan, France); vol. <8> 19; (1910); p. 210 View in Reaxys OH

O

aqueous NaOH-solution N

O O

H 2N

H 2N O

O

o-azobenzoic acid N

HO

O O

Rx-ID: 7456360 View in Reaxys 273/361 Yield

Conditions & References Freundler; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 882 View in Reaxys Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 664; Bulletin de la Societe Chimique de France; vol. <3> 33; (1905); p. 1165 View in Reaxys Carre; Annales de Chimie (Cachan, France); vol. <8> 6; (1905); p. 412; Annales de Chimie (Cachan, France); vol. <8> 19; (1910); p. 210 View in Reaxys H N

HO

O

O

O

O

O H 2N

O

NH

O O

O

O

N H HO

O

OH

Rx-ID: 133522 View in Reaxys 274/361 Yield

Conditions & References T= 130 - 135 °C , im Rohr Freundler; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 882 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Bredt; Hof; Chemische Berichte; vol. 33; (1900); p. 29 View in Reaxys Schmidt,G.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 36; (1887); p. 374 View in Reaxys Erdmann,E.; Chemische Berichte; vol. 32; (1899); p. 2171 View in Reaxys OH

O

OH

H 2N

O

O

N N

O N

HO

HO

O

O

Rx-ID: 282905 View in Reaxys 275/361 Yield

Conditions & References With sodium hydroxide, ethanol, zinc Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 289; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 450 View in Reaxys O H 2N

O

N O

O

HO

O

Rx-ID: 294398 View in Reaxys 276/361 Yield

Conditions & References With sodium hydroxide, ethanol, zinc Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 289; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 450 View in Reaxys OH

O N OH

O

O O

zinc dust

O N

O O

O

OH

H 2N O

N N

HO

HO

O

Rx-ID: 7449639 View in Reaxys 277/361 Yield

Conditions & References Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 289; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 450 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

OH

Cl

H 2N

H N

O

alkali

Cl O

HO

Rx-ID: 7917284 View in Reaxys 278/361 Yield

Conditions & References Gaertner; Justus Liebigs Annalen der Chemie; vol. 336; (1904); p. 244 View in Reaxys

H 2N

NH O

Cl

H N H

2.4-dioxo-quinazoline tetrahydride

N H HO

O

NH 2

H 2N

O

Rx-ID: 8252023 View in Reaxys 279/361 Yield

Conditions & References Koenig; Journal fuer Praktische Chemie (Leipzig); vol. <2> 69; (1904); p. 20 View in Reaxys

O

O H 2N

N

N

N

OH

O

OH O

N N

HO

HO

O

Rx-ID: 291221 View in Reaxys 280/361 Yield

Conditions & References With sodium hydroxide Bamberger; Demuth; Chemische Berichte; vol. 36; (1903); p. 374 View in Reaxys O

O N

H 2N O

O

HO

Rx-ID: 358686 View in Reaxys 281/361 Yield

Conditions & References With sodium hydroxide, zinc Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 523; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 43 View in Reaxys O

H 2N O I

NH

KOH-solution

O

HO O

Rx-ID: 5673665 View in Reaxys 282/361 Yield

Conditions & References Tscherniac; Chemische Berichte; vol. 36; (1903); p. 218

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys O N

N

O

N

H 2N

N

OH

O

O O

o-azoxybenzoic acid HO

O

Rx-ID: 7456371 View in Reaxys 283/361 Yield

Conditions & References Bamberger; Demuth; Chemische Berichte; vol. 36; (1903); p. 374 View in Reaxys O

O N

zinc dust

O

alcoholic NaOH-solution

O

NH 2

N

H 2N O

O

N

HO O

o-indazyl-benzoic acid Rx-ID: 7924420 View in Reaxys 284/361 Yield

Conditions & References Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 523; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 43 View in Reaxys

O

OH

O H 2N

N H N

NH 2

O

O O

O

HO

O

Rx-ID: 326830 View in Reaxys 285/361 Yield

Conditions & References Anschuetz; Schmidt; Greiffenberg; Chemische Berichte; vol. 35; (1902); p. 3478 View in Reaxys

N

O

OH

N

aqueous-alcoholic KOH-solution O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

OH H 2N

H N

NH 2

O

O

HO

Rx-ID: 5673689 View in Reaxys 286/361 Yield

Conditions & References Anschuetz; Schmidt; Greiffenberg; Chemische Berichte; vol. 35; (1902); p. 3478 View in Reaxys H 2N

O

H

O

H O

N O

HO

Rx-ID: 7443797 View in Reaxys 287/361 Yield

Conditions & References durch Einw. eines elektrisch erhitzten Gluehkoerpers Loeb; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 8; (1902); p. 775 View in Reaxys

O

OH H 2N

H N

O

3-<2-carboxy-phenyl>-4-oxo-2-methyl-quinazoline dihydride NH 2

O

HO

Rx-ID: 7443813 View in Reaxys 288/361 Yield

Conditions & References With potassium carbonate Anschuetz; Schmidt; Greiffenberg; Chemische Berichte; vol. 35; (1902); p. 3478 View in Reaxys

N

O

O

N

H 2N

N

N

O

O O

HO

O

Rx-ID: 144768 View in Reaxys 289/361 Yield

Conditions & References Bamberger; Demuth; Chemische Berichte; vol. 34; (1901); p. 1338 View in Reaxys

N

O

H 2N

N N

O

HO

Rx-ID: 144772 View in Reaxys 290/361 Yield

Conditions & References With sodium hydroxide Bamberger; Demuth; Chemische Berichte; vol. 34; (1901); p. 1338

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys

N N OH

Cl

N

H

tin dichloride O

H 2N O HN H 2N

HO

Rx-ID: 5687985 View in Reaxys 291/361 Yield

Conditions & References unter Eiskuehlung Mehner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 63; (1901); p. 244; Journal fuer Praktische Chemie (Leipzig); vol. <2> 65; (1902); p. 533 View in Reaxys

N

OH N

NH

N

KOH-solution N OH

H 2N

N

O N

H 2N

N

O

O

HO

Rx-ID: 8255418 View in Reaxys 292/361 Yield

Conditions & References Bamberger; Demuth; Chemische Berichte; vol. 34; (1901); p. 1338 View in Reaxys

OH H 2N

O

O

zinc dust

O

disulfite

N

HO

O

Rx-ID: 7443811 View in Reaxys 293/361 Yield

Conditions & References Goldberger; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 1014 View in Reaxys

O N

aqueous concentrated NaOH-solution

O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

NH H 2N N O O

azoxybenzoic acid HO

HO

Rx-ID: 7451160 View in Reaxys 294/361 Yield

Conditions & References T= 150 °C Preuss; Binz; ; vol. 13; (1900); p. 385 View in Reaxys Patent; Bad. Anilin- u. Sodaf.; DE114839 View in Reaxys

O

concentrated alcoholic NaOH-solution

N O

NH H 2N N O O

azoxybenzoic acid HO

HO

Rx-ID: 7451161 View in Reaxys 295/361 Yield

Conditions & References Preuss; Binz; ; vol. 13; (1900); p. 385 View in Reaxys Patent; Bad. Anilin- u. Sodaf.; DE114839 View in Reaxys H N

O

H 2N O

O HO

O

Rx-ID: 133605 View in Reaxys 296/361 Yield

Conditions & References With hydrogenchloride Kolbe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 30; (1884); p. 124 View in Reaxys With sodium carbonate, Ansaeuern der Loesung Erdmann,E.; Chemische Berichte; vol. 32; (1899); p. 2166 View in Reaxys

H 2N

O O

O

N H HO

O

OH

Rx-ID: 322876 View in Reaxys 297/361 Yield

Conditions & References With potassium carbonate

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Erdmann,E.; Chemische Berichte; vol. 32; (1899); p. 2171 View in Reaxys O

O H 2N

NH

O O

O

HO

Rx-ID: 324176 View in Reaxys 298/361 Yield

Conditions & References With potassium carbonate Erdmann,E.; Chemische Berichte; vol. 32; (1899); p. 2171 View in Reaxys

H 2N

O O

O

alcoholic KOH-solution

N H

HO

O

OH

Rx-ID: 7443798 View in Reaxys 299/361 Yield

Conditions & References Erdmann,E.; Chemische Berichte; vol. 32; (1899); p. 2171 View in Reaxys O

O H 2N

NH

O O

O

alcoholic KOH-solution HO

Rx-ID: 7443799 View in Reaxys 300/361 Yield

Conditions & References Erdmann,E.; Chemische Berichte; vol. 32; (1899); p. 2171 View in Reaxys

O

OH H 2N

Cl

O

H N

H

O

HO

O

HO

Rx-ID: 6683395 View in Reaxys 301/361 Yield

Conditions & References T= 110 - 120 °C Fischer,E.; Chemische Berichte; vol. 29; (1896); p. 2063 View in Reaxys O H 2N N O

O

ammonium sulfide HO

HO

Rx-ID: 7443800 View in Reaxys 302/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References T= 100 °C Fischer,E.; Chemische Berichte; vol. 29; (1896); p. 2063 View in Reaxys

N H

Cl

O

OH

N

H

N

O

OH

H 2N O

ang.naphthophenazine HO

Rx-ID: 8268178 View in Reaxys 303/361 Yield

Conditions & References Marshall; Chemische Berichte; vol. 28; (1895); p. 338 View in Reaxys O O

O H 2N

OH O

Cl

H HN HO

O

O

OH

Rx-ID: 8252020 View in Reaxys 304/361 Yield

Conditions & References Lagodzinski; Hardine; Chemische Berichte; vol. 27; (1894); p. 3074 View in Reaxys OH

O

O

H 2N

OH N

O

diluted mineral acid HO

O OH O

Rx-ID: 8252021 View in Reaxys 305/361 Yield

Conditions & References Lagodzinski; Hardine; Chemische Berichte; vol. 27; (1894); p. 3074 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O O

O H 2N

OH O

KOH-solution

HN

HO

O

O

OH

Rx-ID: 8252022 View in Reaxys 306/361 Yield

Conditions & References Lagodzinski; Hardine; Chemische Berichte; vol. 27; (1894); p. 3074 View in Reaxys O

NH

potassium hypobromite

alkali hydroxide

O

H 2N O

HO

Rx-ID: 5673669 View in Reaxys 307/361 Yield

Conditions & References Hoogewerff; van Dorp; Recueil des Travaux Chimiques des Pays-Bas; vol. 10; (1891); p. 6 View in Reaxys

N N

concentrated alkaline solution

NH

O H 2N O

nitrogen HO

Rx-ID: 5739941 View in Reaxys 308/361 Yield

Conditions & References Finger; Journal fuer Praktische Chemie (Leipzig); vol. <2> 37; (1888); p. 441 View in Reaxys

N N N

KOH-solution

O H 2N O

methanol(?)

nitrogen

HO

Rx-ID: 5739997 View in Reaxys 309/361 Yield

Conditions & References Weddige; Finger; Journal fuer Praktische Chemie (Leipzig); vol. <2> 35; (1887); p. 262

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

View in Reaxys Finger; Journal fuer Praktische Chemie (Leipzig); vol. <2> 37; (1888); p. 441 View in Reaxys O

OH

H 2N H N

O

Cl

Cl

HO

O

OH

H

H 2N 2 O O

HO

Rx-ID: 5914157 View in Reaxys 310/361 Yield

Conditions & References T= 150 °C , im Druckrohr Schmidt,G.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 36; (1887); p. 374 View in Reaxys

O

OH H 2N

H N

O

O

HO

Rx-ID: 72572 View in Reaxys 311/361 Yield

Conditions & References With hydrogenchloride, T= 110 °C Doebner; v. Miller; Chemische Berichte; vol. 19; (1886); p. 1198 View in Reaxys

O O

OH

N

permanganate

N H OH

O

O H 2N

N

O

OH

6-oxy-isocinchomeronic acid HO

Rx-ID: 5695670 View in Reaxys 312/361 Yield

Conditions & References Weidel; Strache; Monatshefte fuer Chemie; vol. 7; (1886); p. 289 View in Reaxys

O

OH N

N H

O

alkaline permanganate solution

O HO

O OH

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

isocinchomeronic acid HO

Rx-ID: 5735850 View in Reaxys 313/361 Yield

Conditions & References Weidel; Strache; Monatshefte fuer Chemie; vol. 7; (1886); p. 289 View in Reaxys

O

O

N

OH

N OH

permanganate

N

H 2N O

kyklothraustinic acid HO

6-oxy-isocinchomeronic acid Rx-ID: 5736390 View in Reaxys 314/361 Yield

Conditions & References Weidel; Strache; Monatshefte fuer Chemie; vol. 7; (1886); p. 289 View in Reaxys

O N

permanganate

N H O

alkali

OH

H 2N O

pyridanthranilic acid

isocinchomeronic acid

HO

Rx-ID: 5743706 View in Reaxys 315/361 Yield

Conditions & References Weidel; Strache; Monatshefte fuer Chemie; vol. 7; (1886); p. 289 View in Reaxys

N

N

alkali

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permanganate

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

isocinchomeronic acid

pyridanthrilic acid

HO

Rx-ID: 5743707 View in Reaxys 316/361 Yield

Conditions & References Weidel; Strache; Monatshefte fuer Chemie; vol. 7; (1886); p. 289 View in Reaxys O

OH

O

H 2N

HO

H N

O O

HO

O

O

OH HO

Rx-ID: 395671 View in Reaxys 317/361 Yield

Conditions & References Friedlaender; Ostermaier; Chemische Berichte; vol. 15; (1882); p. 335 View in Reaxys Kretschy; Monatshefte fuer Chemie; vol. 5; (1884); p. 30 View in Reaxys H N

O

H 2N

HO

O

Cl

H

OH H 2N 2

O O HO

O

Rx-ID: 5684125 View in Reaxys 318/361 Yield

Conditions & References Kolbe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 30; (1884); p. 86,472 View in Reaxys H N

O

H 2N

O

HO

HO

O

OH

OH H 2N 2

S OO

O HO

O

Rx-ID: 5684126 View in Reaxys 319/361 Yield

Conditions & References Kolbe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 30; (1884); p. 86,472 View in Reaxys H N

O

H 2N

HO H

O

H

OH

O

H 2N 2

O

O HO

O

Rx-ID: 5684127 View in Reaxys 320/361 Yield

Conditions & References Kolbe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 30; (1884); p. 86,472 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N H 2N

O O

Br

sodium amalgam

HO HO

Br

Rx-ID: 7443804 View in Reaxys 321/361 Yield

Conditions & References Huebner; Smith; Justus Liebigs Annalen der Chemie; vol. 222; (1884); p. 188 View in Reaxys H N

H 2N

HO

O O

permanganate O

OH HO

Rx-ID: 5673693 View in Reaxys 322/361 Yield

Conditions & References Hoffmann; Koenigs; Chemische Berichte; vol. 16; (1883); p. 735 View in Reaxys H 2N

N O

O

HO

Rx-ID: 338734 View in Reaxys 323/361 Yield

Conditions & References With sodium hydroxide Friedlaender; Henriques; Chemische Berichte; vol. 15; (1882); p. 2105 View in Reaxys

N

potassium permanganate

H 2N

HO

O O

O

O

OH

N H

HO

O

OH

Rx-ID: 5711876 View in Reaxys 324/361 Yield

Conditions & References Doebner; v. Miller; Chemische Berichte; vol. 15; (1882); p. 3077 View in Reaxys O

OH

O

H 2N

HO

H N

Cl

H

O O

OH

O

O

O

OH HO

Rx-ID: 7443814 View in Reaxys 325/361 Yield

Conditions & References Bayer; Chemische Berichte; vol. 15; (1882); p. 778 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

O

N H HO

O

OH

Rx-ID: 820002 View in Reaxys 326/361 Yield

Conditions & References With hydrogenchloride Bedson; Journal of the Chemical Society; vol. 37; (1880); p. 752 View in Reaxys H 2N O

phthalylhydroxylamine HO

Rx-ID: 5820553 View in Reaxys 327/361 Yield

Conditions & References With potassium hydroxide, ethanol Lassar-Cohn; Justus Liebigs Annalen der Chemie; vol. 205; (1880); p. 295 View in Reaxys With water, sodium carbonate Patent; Basler chem. Fabr.; DE130301 View in Reaxys H 2N

O

Br H 2N

N

O O

O O

sodium amalgam HO HO

O

Br

Rx-ID: 5820554 View in Reaxys 328/361 Yield

Conditions & References Greiff; Chemische Berichte; vol. 13; (1880); p. 288 View in Reaxys

H 2N O

O

Cl

OH

H O

N H HO

O

OH

Rx-ID: 5853524 View in Reaxys 329/361 Yield

Conditions & References Bedson; King; Journal of the Chemical Society; vol. 37; (1880); p. 755 View in Reaxys

NH

H

H

O–

O

O

S

K+

potassium permanganate

O

O

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

H 2N O

potassium sulfate HO

Rx-ID: 8285777 View in Reaxys 330/361 Yield

Conditions & References Baumann; Tiemann; Chemische Berichte; vol. 12; (1879); p. 1192 View in Reaxys

H 2N

H 2N O

nascent hydrogen

O I

HO OH

Rx-ID: 5820552 View in Reaxys 331/361 Yield

Conditions & References Grothe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 18; (1878); p. 326 View in Reaxys O

NH 2

H 2N

I

O

HO

nascent hydrogen HO

Rx-ID: 7443801 View in Reaxys 332/361 Yield

Conditions & References Grothe; Journal fuer Praktische Chemie (Leipzig); vol. <2> 18; (1878); p. 326 View in Reaxys OH

H 2N H 2N

Br

O

O

Cl

O

H

Br

tin

O N

HO

Br

HO

Br

O

Rx-ID: 8252024 View in Reaxys 333/361 Yield

Conditions & References Huebner; Angerstein; Justus Liebigs Annalen der Chemie; vol. 158; (1871); p. 10 View in Reaxys Huebner; Smith; Chemische Berichte; vol. 10; (1877); p. 1706; Justus Liebigs Annalen der Chemie; vol. 222; (1884); p. 188 View in Reaxys NH 2 O

O

H 2N O

S HO

HO

Rx-ID: 319879 View in Reaxys 334/361 Yield

Conditions & References With potassium carbonate, beim Schmelzen Hayduck; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 217; Justus Liebigs Annalen der Chemie; vol. 174; (1874); p. 352 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

NH 2

H 2N

O O

O

potassium hydroxide

S

HO

HO

Rx-ID: 7443803 View in Reaxys 335/361 Yield

Conditions & References beim Schmelzen Hayduck; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 217; Justus Liebigs Annalen der Chemie; vol. 174; (1874); p. 352 View in Reaxys OH H 2N

O

Cl

O

H

tin

O N

HO

O

Rx-ID: 7443810 View in Reaxys 336/361 Yield

Conditions & References Beilstein; Kuhlberg; Justus Liebigs Annalen der Chemie; vol. 163; (1872); p. 126 View in Reaxys O

NH 2

H 2N

Br

O

HO

HO

Rx-ID: 404283 View in Reaxys 337/361 Yield

Conditions & References With sodium amalgam Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys

H 2N

H 2N O

O Br HO

OH

Rx-ID: 763774 View in Reaxys 338/361 Yield

Conditions & References With sodium amalgam Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys O

H 2N NH

O

HN

HO O

Rx-ID: 820502 View in Reaxys 339/361 Yield

Conditions & References With potassium hydroxide

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Fritzsche; Justus Liebigs Annalen der Chemie; vol. 39; (1841); p. 79 View in Reaxys With manganese(IV) oxide, potassium hydroxide Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys Liebig; Justus Liebigs Annalen der Chemie; vol. 39; (1841); p. 91 View in Reaxys OH H 2N

H 2N

O O

Cl

H

O

tin N

O Br

Br HO

OH

O

Rx-ID: 7447406 View in Reaxys 340/361 Yield

Conditions & References Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys HO

O

NH 2

H 2N

Br

Cl

H

O

tin O

N

HO

O

Br HO O

Rx-ID: 8252026 View in Reaxys 341/361 Yield

Conditions & References Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys OH H 2N

O O

O N

Br HO

O

Rx-ID: 22296561 View in Reaxys 342/361 Yield

Conditions & References Reaction Steps: 2 1: tin; hydrochloric acid 2: sodium amalgam With hydrogenchloride, tin, sodium amalgam Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys Reaction Steps: 2 1: zinc; diluted sulfuric acid; alcohol 2: sodium amalgam With sodium amalgam, ethanol, sulfuric acid, zinc Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

HO H 2N O O O

N

Br HO O

Rx-ID: 22303590 View in Reaxys 343/361 Yield

Conditions & References Reaction Steps: 2 1: tin; hydrochloric acid 2: sodium amalgam With hydrogenchloride, tin, sodium amalgam Huebner; Petermann; Justus Liebigs Annalen der Chemie; vol. 149; (1869); p. 142 View in Reaxys NH 2 O

O

H 2N

O

O

S OH

HO

HO

Rx-ID: 324500 View in Reaxys 344/361 Yield

Conditions & References With sodium amalgam Patent; Kalle and Co.; DE129165 View in Reaxys durch elektrolytische Reduktion in neutraler oder schwach saurer Loesung Patent; Kalle and Co.; DE146716 View in Reaxys Electrolysis Patent; Kalle and Co.; DE146716 View in Reaxys O

OH

O

H 2N

HO

O

N H HO

Rx-ID: 371166 View in Reaxys 345/361 Yield

Conditions & References With water Patent; Hoechster Farbw.; DE136788 View in Reaxys With alkali carbonate, water Patent; Hoechster Farbw.; DE136788 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

OH O

O HO

OH

O

H 2N

H N O

N

O

HO

HO

O HO

Rx-ID: 396882 View in Reaxys 346/361 Yield

Conditions & References bei der Behandlung mit Oxydationsmitteln Patent; B.A.S.F.; DE149346 View in Reaxys OH H 2N

Cl

Cl

O

O HN

Cl

O

Cl

H 2N

N

HO

O

Rx-ID: 721163 View in Reaxys 347/361 Yield

Conditions & References T= 180 °C , im Autoklaven Walther; Journal fuer Praktische Chemie (Leipzig); vol. <2> 53; p. 448 View in Reaxys H 2N

H 2N O N

K

Br

HO

Rx-ID: 779940 View in Reaxys 348/361 Yield

Conditions & References With ethanol, copper(l) cyanide, T= 210 °C Patent; Rosenmund; Struck; DE327049; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 13; p. 270 View in Reaxys O H 2N O

OH

N

OH

alkali carbonate HO

O

Rx-ID: 5673659 View in Reaxys 349/361 Yield

Conditions & References die Ausgangsstoffe sind die Alkalisalze Patent; Basler Chem.Fabr.; DE130302; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 152 View in Reaxys O H 2N

N

OH

H

O

H O

alkali carbonate HO

O

Rx-ID: 5673660 View in Reaxys 350/361

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Yield

Conditions & References die Ausgangsstoffe sind die Alkalisalze Patent; Basler Chem.Fabr.; DE130302; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 152 View in Reaxys O H 2N O

N

Cl

diluted NaOH-solution HO

O

Rx-ID: 5673664 View in Reaxys 351/361 Yield

Conditions & References Patent; Hoechster Farbw.; DE133950; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 157 View in Reaxys O H 2N

N

H

OH

O

H

sodium carbonate

O

HO

O

Rx-ID: 5673671 View in Reaxys 352/361 Yield

Conditions & References Patent; Basler Chem.Fabr.; DE130301; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 151 View in Reaxys O

H 2N O NH

sodium hypochlorite

alkali hydroxide HO

O

Rx-ID: 5673672 View in Reaxys 353/361 Yield

Conditions & References Patent; BASF; DE55988; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 2; p. 546 View in Reaxys O

O

N

H

O

H

potassium hydroxide

O

O H 2N O O

HO HO

Rx-ID: 5690851 View in Reaxys 354/361 Yield

Conditions & References Brockmann; View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

Cl

H

H

H 2N

O

N

O

copper H HO

HO

Rx-ID: 5820550 View in Reaxys 355/361 Yield

Conditions & References T= 125 °C , unter Druck Patent; Hoechster Farbw.; DE145604 View in Reaxys

Cl

H

H 2N

H O

N

O

copper

N H

H HO

HO

HO

O

O

OH

Rx-ID: 5831869 View in Reaxys 356/361 Yield

Conditions & References T= 125 °C , unter Druck Patent; Hoechster Farbw.; DE145605 View in Reaxys NH 2 O

O

H 2N

O

H

O

H

sodium amalgam

O

S OH

HO

HO

Rx-ID: 7443805 View in Reaxys 357/361 Yield

Conditions & References Patent; Kalle and Co.; DE129165 View in Reaxys O

OH

O

H 2N

HO

H N H

O

H

alkali carbonate

O

HO

Rx-ID: 7917283 View in Reaxys 358/361 Yield

Conditions & References Patent; Hoechster Farbw.; DE136788 View in Reaxys O

OH

O HO

H 2N

H N H

O

H O

alkali HO

Rx-ID: 7917285 View in Reaxys 359/361 Yield

Conditions & References Patent; Hoechster Farbw.; DE136788 View in Reaxys

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2-Aminobenzoic acid (Anthranilic acid) [C7H7NO2]

O

NH 2

H 2N

HO

H

O

O O

diluted NaOH-solution

H

O HO

Rx-ID: 7917286 View in Reaxys 360/361 Yield

Conditions & References T= 10 - 15 °C Patent; Kalle and Co.; DE375616; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 447 View in Reaxys O

H N

OH

H N

sodium sulfite O

OH H 2N O

neutral 'δ-sulfomethylanthranilate ' sodium HO

Rx-ID: 7924211 View in Reaxys 361/361 Yield

Conditions & References Patent; Bad. Anilin- u. Sodaf.; DE156760 View in Reaxys

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