Phenylacetic acid (2-phenylacetic acid, PAA) [CAS 103-82-2; InChIKey WLJVXDMOQOGPHL-UHFFFAOYS

Query Query

Results

Date

325 reactions in Reaxys

2016-04-10 14h:10m:17s (EST)

325 reactions in Reaxys

2016-04-10 14h:37m:07s (EST)

HO

1. Query

O

Search as: As drawn 2. Query

(1. Query) AND NOT itemno in (1)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

1/96

2016-04-10 14:47:02

2H

HO

2H

O

HO

O

Rx-ID: 1623767 View in Reaxys 1/325 Yield 98 %

Conditions & References in water-d2, Time= 9h, T= 200 °C Flakus, Henryk T.; Chelmecki, Michal; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 58; nb. 9; (2002); p. 1867 - 1880 View in Reaxys

91 %

2.1 :Step 1 Phenylacetic acid-d2: A mixture of phenylacetic acid (5.00 g; 36.72 mmol), anhydrous potassium carbonate (20.30 g; 146.88 mmol) and deuterium oxide (30 mL) was heated at about 100° C. for about 24 hours. The reaction mixture was cooled to about 0° C., acidified to pH 2 with 6N hydrochloric acid, and then extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. This process was repeated two more times to give the title compound as a white solid (4.60 g; 91percent). 1H NMR (400 MHz, CDCl3) δ 7.21-7.36 (m, 5H); IR (film) υ 3061, 1700, 1497, 1448, 1408, 1294 cm-1; MS 137 (M-1).

Stage 1: With water-d2, potassium carbonate, Time= 24h, T= 100 °C Stage 2: With hydrogenchloride in water, T= 0 °C , pH= 2 Patent; AUSPEX PHARMACEUTICALS, INC.; US2010/16365; (2010); (A1) English View in Reaxys

90 %

With water-d2, sodium hydride, Time= 96h, T= 100 °C , Heating, Addition Ishii, Shingo; Zhao, Shikai; Helquist, Paul; Journal of the American Chemical Society; vol. 122; nb. 24; (2000); p.

5897 - 5898 View in Reaxys With NaOD, water-d2, Time= 24h, T= 100 °C Orfanopoulos; Smonou; Foote; Journal of the American Chemical Society; vol. 112; nb. 9; (1990); p. 3607 - 3614 View in Reaxys With hydrogenchloride, diclazuril, water-d2, 1.) reflux, 142 h; 2.) reflux, 72 h, Yield given. Multistep reaction Werstiuk, Nick Henry; Timmins, George; Canadian Journal of Chemistry; vol. 64; (1986); p. 1072 - 1076 View in Reaxys With NaOD, water-d2, Time= 24h, T= 120 °C , sealed tube Raftery, Mark J.; Bowie, John H.; Sheldon, John C.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1988); p. 563 - 570 View in Reaxys With water-d2, T= 100 °C Orfanopoulos, Michael; Foote, Christopher S.; Journal of the American Chemical Society; vol. 110; nb. 19; (1988); p. 6583 - 6584 View in Reaxys With water-d2, sodium carbonate, Raney Co-Al, Time= 2h, T= 90 °C Tsukinoki, Takehito; Ishimoto, Keiko; Mukumoto, Mamoru; Suzuki, Michio; Kawaji, Takatoshi; Nagano, Yoshiaki; Tsuzuki, Hirohisa; Mataka, Shuntaro; Tashiro, Masashi; Journal of Chemical Research - Part S; nb. 1; (1996); p. 66 - 67 View in Reaxys

HO O

poly(phenylacetic acid) Rx-ID: 29004170 View in Reaxys 2/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/96

2016-04-10 14:47:02

Yield 100 %

Conditions & References 4 :Example 4 Phenyl acetic acid (5 g, 0.0367 mol) was added to a RB flask followed by phosphorus pentoxide (10.43 g, 0.0367 mol). The flask was fitted with a drying tube after adding 45 ml of methane sulfonic acid. The mixture was heated at 80° C. for 3 h. Then the temperature was raised to 110° C. After 1.5 h a swollen mass was obtained. Another 20 ml of methane sulfonic acid was added. The mass swelled still further. Another 20 ml of methane sulfonic acid was added and held at 110° C. for 24 h. The flask was then cooled down to room temperature and the contents of the flask were transferred into 2000 ml of water. The solid obtained was filtered, washed repeatedly with hot water followed by water at ambient temperature until it showed neutral pH and then dried in a vacuum oven for two days at 50° C. The polymer thus obtained was insoluble in THF and other solvents. Yield 4.3 g (quantitative). IR (KBr) cm-1: 3431(b), 3064(w), 1678(s), 1603(ss), 1417(w), 1361(w), 1298(w), 1194(ss), 1049(s), 960(s), 779(s), 698(w) and 532(w).

With methanesulfonic acid, phosphorus pentoxide, Time= 28.5h, T= 80 - 110 °C Patent; Agency for Science, Technology and Research; US2005/272905; (2005); (A1) English View in Reaxys

92.2 %

3 :Example 3 Phenyl acetic acid (10 g, 0.0734 mol) was added to a RB flask followed by phosphorus pentoxide (21 g, 0.0739 mol). The flask was fitted with a drying tube after adding 90 ml of methane sulfonic acid. The mixture was heated to 70° C. and held for 24 h. The flask was then cooled down to room temperature and the contents of the flask were poured into 2000 ml water. The solid obtained was filtered, washed repeatedly with hot water followed by water at ambient temperature until it showed neutral pH and then dried. After drying the polymer was dissolved in THF and precipitated in hexane. The precipitate was filtered and dried in a vacuum oven for two days at 50° C. Yield 8 g (92.2percent). GPC (Polystyrene standards; THF eluent): Number average molecular weight, Mn=24330; Weight average molecular weight, Mw=63477. IR (KBr) cm-1: 3453(b), 3058(s), 3027(s), 1761(s), 1711(w), 1677(s), 1630(w), 1601(s), 1495(ss), 1444(w), 1411(s), 1368(s), 1312(s), 1223(s), 1180(s), 1148(s), 1113(s), 965(s), 758(s), 700(ss) and 521(s). [b=broad, s=sharp, ss=sharp and strong, w=weak].

With methanesulfonic acid, phosphorus pentoxide, Time= 24h, T= 70 °C Patent; Agency for Science, Technology and Research; US2005/272905; (2005); (A1) English View in Reaxys

57.63 %

2 :Example 2 Phenyl acetic acid (10 g, 0.0734 mol) was added to a RB flask followed by phosphorus pentoxide (21 g, 0.0739 mol). The flask was fitted with a drying tube after adding 120 ml of methane sulfonic acid. The mixture was heated to 55° C. and held for 48 h. The flask was then cooled down to room temperature and the contents of the flask were poured into 2000 ml water. The solid obtained was filtered, washed repeatedly with hot water and then with water at ambient temperature until it showed neutral pH and then dried. After drying the polymer was dissolved in THF and precipitated in hexane. The precipitate was filtered and dried in a vacuum oven maintained at 50° C. for two days. Yield 5 g (57.63percent). GPC (Polystyrene standards; THF eluent): Number average molecular weight, Mn=10829; Weight average molecular weight, Mw=43898. IR (KBr) cm-1: 3449(b), 3058(s), 3028(s), 1758(s), 1708(w), 1677(s), 1630(s), 1601(s), 1495(ss), 1367(s), 1222(s), 1180(s), 1148(s), 1113(s), 757(s), 700(ss) and 521 (s).

With methanesulfonic acid, phosphorus pentoxide, Time= 48h, T= 55 °C Patent; Agency for Science, Technology and Research; US2005/272905; (2005); (A1) English View in Reaxys

6H O 2

HO O

Zn 2+

O

O O

2

N O–

O–

Zn 2+

Rx-ID: 38684153 View in Reaxys 3/325 Yield 70 %

Conditions & References 2.3.1. [Zn(L1)2] (1).

General procedure: The sodium salt of HL1 (4-nitrophenylacetic acid) was prepared by dropwise addition of methanolic solution of 4-nitrophenyl acetic acid (0.318 g, 2 mM) to an aqueous solution of sodium bicarbonate (0.168 g, 2 mM) with constant stirring at 50 °C. After neutralization, the aqueous solution of zinc(II) nitrate hexahydrate (0.297 g, 1 mM) was added dropwise. The reaction mixture was stirred for 2 h at 50 °C. The product was filtered at room temperature, washed thoroughly with distilled water, and air dried. Yield: 84percent,

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/96

2016-04-10 14:47:02

Stage 1: With sodium hydrogencarbonate in methanol, water, T= 50 °C Stage 2: in methanol, water, Time= 2h, T= 50 °C Ali, Nida; Tahir, Muhammad Nawaz; Ali, Saqib; Iqbal, Muhammad; Munawar, Khurram Shahzad; Perveen, Sajida; Journal of Coordination Chemistry; vol. 67; nb. 7; (2014); p. 1290 - 1308 View in Reaxys

N

HO

N

6H O 2

N

O O

O

Zn 2+

N

N

O

2

O–

O–

Zn 2+

Rx-ID: 38684154 View in Reaxys 4/325 Yield 78 %

Conditions & References 2.3.2. [Zn(L1)2(phen)·H2O]·H2O (2).

General procedure: The sodium salt of HL1 was prepared by the same procedure as that for 1. After 2 h stirring following the addition of zinc(II) nitrate hexahydrate(0.297 g, 1 mM), 1,10-phenanthroline (0.180 g, 1 mM) was added.

Stirring was continued for another 3 h under the same reaction conditions. The final product was filtered, washed thoroughly with distilled water, and air dried. The solid was recrystallized in methanol. Yield: 82percent, Stage 1: With sodium hydrogencarbonate in methanol, water, Time= 2h, T= 50 °C Stage 2: in methanol, water, Time= 3h, T= 50 °C Ali, Nida; Tahir, Muhammad Nawaz; Ali, Saqib; Iqbal, Muhammad; Munawar, Khurram Shahzad; Perveen, Sajida; Journal of Coordination Chemistry; vol. 67; nb. 7; (2014); p. 1290 - 1308 View in Reaxys

2H

HO O

HO O

Rx-ID: 1623768 View in Reaxys 5/325 Yield

Conditions & References With n-butyllithium, water-d2, 1.) hexanes, -78 deg C, 1 h, 2.) 0 deg C, Yield given. Multistep reaction Silks III, Louis A.; Dunlap, R. Bruce; Odom, Jerome D.; Journal of the American Chemical Society; vol. 112; nb.

12; (1990); p. 4979 - 4982 View in Reaxys With water-d2, 2-[4-(2-hydroxyethyl)-1-piperazinyl] ethanesulfonic acid, Time= 48h, T= 37 °C , pH= 8, Enzymatic reaction Kourist, Robert; Miyauchi, Yusuke; Uemura, Daisuke; Miyamoto, Kenji; Chemistry - A European Journal; vol.

17; nb. 2; (2011); p. 557 - 563 View in Reaxys

> 90 %Spectr.

4.4. Metalation of arylacetic acids 2, and reaction with electrophiles. General procedure General procedure: To 5 mL of a 0.24 M solution of diorganometal 1b or 1c (1.2 mmol), chilled at 0 °C, was added a solution of the appropriate arylacetic acid 2 (1.1 mmol) dissolved in 5 mL of dry THF, and the resulting mixture was vigorously stirred for 2 h at 0 °C. To the resulting dark brown mixture, chilled at the same temperature, were added 1.7 mmol of the appropriate electrophile. The resulting mixture was vigorously stirred and allowed to reach rt overnight, after which time it was quenched by slow dropwise addition of H2O (15 mL). The organic solvent was evaporated in vacuo and the resulting mixture was extracted with CH2Cl2 (3.x.10 mL). The aqueous phase was acidified with 1 N HCl, extracted with CH2Cl2 (3.x.10 mL), and the organic phases were collected, washed with H2O (1.x.10 mL), brine (10 mL), dried (Na2SO4), and the solvent was evaporated. Crude reaction products were purified and characterized as reported below. The reaction mixture containing crude β-hydroxyacid 2df was quenched by adding it to 15 mL of 10percent HCl containing about 15 g of crushed ice,14 and worked up as described above. After evaporation of the solvent, the resulting crude material was purified and characterized as reported below. Quenching with D2O was realized as described in the above paragraph.

Stage 1: With 1,2-disodiostilbene in tetrahydrofuran, Time= 2h, T= 0 °C , Inert atmosphere

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/96

2016-04-10 14:47:02

Stage 2: With water-d2 in tetrahydrofuran, T= 0 °C , Inert atmosphere Stage 3: With hydrogenchloride in water, regioselective reaction Azzena, Ugo; Dettori, Giovanna; Pisano, Luisa; Pittalis, Mario; Tetrahedron; vol. 67; nb. 19; (2011); p. 3470 3475 View in Reaxys 2H 2H

HO O

Rx-ID: 11083783 View in Reaxys 6/325 Yield 85 %

Conditions & References With Oxonereg;, sodium hydrogencarbonate, [Mn(2,6-Cl2-TPP)Cl] in water, acetonitrile Chan, Wing-Kei; Ho, Chi-Ming; Wong, Man-Kin; Che, Chi-Ming; Journal of the American Chemical Society; vol.

128; nb. 46; (2006); p. 14796 - 14797 View in Reaxys

O

PdCl2 (PPH3)2

Cl

K+

O–

Rx-ID: 25045005 View in Reaxys 7/325 Yield 94%

Conditions & References 9 : EXAMPLE 9 EXAMPLE 9 As in Example 8, the following materials were used: Reactor: 50.0 mg PdCl2 (PPh3)2; 0.202 g PPh3; 33.73 g benzyl chloride; 4.7 g methanol.

KOH solution: 40.4 g KOH (87.8percent); 106.1 g methanol.

PPh3 solution: 0.667 g PPh3; 56.2 g methanol.

Under the reaction conditions described in Example 1, 128 ml of the KOH solution, and 19.4 ml of the PPh3 solution were delivered to the reactor over a 45-minute period.

After five additional minutes, the reactor was cooled and vented.

LC and GC analyses revealed that a 94percent yield of potassium phenylacetate was obtained on a 97percent conversion.

With potassium hydroxide, triphenylphosphine in methanol Patent; Stauffer Chemical Company; US4713484; (1987); (A1) English View in Reaxys

2H

O

2

O–

Na +

H

HO

O

Rx-ID: 2428693 View in Reaxys 8/325 Yield

Conditions & References With NaOD, water-d2, Time= 4h, Heating Zamojski, Aleksander; Grzeszczyk, Barbara; Banaszek, Anna; Babinski, Jakub; Bordas, Xavier; et. al.; Carbohydrate Research; vol. 142; (1985); p. 165 - 171 View in Reaxys 57 :Example 57This example illustrates the preparation of compounds 126 and 127 according to the approach provided in Scheme 34. The general method is applicable to other compounds of the present invention. Scheme 34Preparation of 2-phenylacetic-2,2-tf2 acid (117) The following procedure uses methods analogous to those described in Carbohydr. Res., 142:165, 1985. Deuterium oxide (70 g, 3.5 mol, 99 atom percent D) in 500 mL of three-necked flask was cooled to about O 0C with an ice bath. Sodium hydride (17 g, 60percent dispersion in mineral oil, 0.425 mol) was added in portions. After completion of the addition, the mixture was warmed to 25 0C and stirred for 1 hour.

Sodium phenylacetate (60 g, 0.379 mol) was added in one portion. The mixture was then warmed to 80 0C and stir-

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/96

2016-04-10 14:47:02

red for 21 hours. The water was removed in vacuum, and the resulting residue was dried at 80 0C in vacuum for about 4 hours. Analysis of 1H-NMR showed that the D/H ratio was about 90percent. Deuterium oxide (42 g, 2.1 mol) was added to the above residue, and the mixture was stirred at 80 0C for 14 hours before being diluted with 100 mL of water. The solution was neutralized to pH 3-4 with 3 M hydrochloric acid, and the mixture was extracted three times with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to give 57 g of crude product as white solid. 1H- NMR showed that the deuterated incorporation ratio was about 97percent. 1H- NMR (400 MHz, methanol-**,): δ 7.34-7.23 (m, 5H), 3.59 (s, 0.06H).

Stage 1: With water-d2, sodium hydride in mineral oil, T= 0 - 80 °C Stage 2: With water-d2, Time= 14h, T= 80 °C Stage 3: With hydrogenchloride in water, pH= 3 - 4 Patent; THERACOS, INC.; SEED, Brian; LV, Binhua; ROBERGE, Jacques, Y.; CHEN, Yuanwei; PENG, Kun; DONG, Jiajia; XU, Baihua; DU, Jiyan; ZHANG, Lili; TANG, Xinxing; XU, Ge; FENG, Yan; XU, Min; WO2010/9243; (2010); (A1) English View in Reaxys

HO

poly(phenylacetic acid)

O

Rx-ID: 29004169 View in Reaxys 9/325 Yield

Conditions & References

46 %

1 :Example 1 Phosphorus pentoxide (10.42 g, 0.0367 mol) was dissolved with stirring in 50 ml of methane sulfonic acid by heating the mixture at 80° C. in a 250 ml RB flask fitted with a drying tube. After complete dissolution the mixture was cooled down to room temperature. Phenyl acetic acid (5 g, 0.0367 mol) was added and the stirring continued at room temperature. On the 3rd day of stirring at room temperature an aliquot was withdrawn and added to water. A clear solution was obtained. On the 4th day an aliquot was withdrawn from the reaction mixture and added to water. A precipitate was observed. The reaction was terminated by adding the reaction mass into 1000 ml water.

The precipitate was filtered off, washed repeatedly with water until the filtered water showed neutral pH and dried.

The dried solid was then dissolved in tetrahydrofuran (THF) and precipitated in hexane. The purified polymer was then dried in a vacuum oven maintained at 50° C. for two days. Yield 2 g (46percent). GPC (Polystyrene standards; THF eluent): Number average molecular weight, Mn=2275; Weight average molecular weight, Mw=5550. IR (KBr) cm-1: 3440(b), 3059(s), 3028(s), 1758(s), 1711(ss), 1600(ss), 1495(ss), 1444(s), 1412(w), 1370(w), 1332(w), 1223(ss), 1181(w), 1113(ss), 1028(w), 755(s), 699(ss) and 521(w).

With methanesulfonic acid, phosphorus pentoxide, Time= 96h, T= 20 °C Patent; Agency for Science, Technology and Research; US2005/272905; (2005); (A1) English View in Reaxys Br

2H

HO O

HO O

Rx-ID: 30764685 View in Reaxys 10/325 Yield

Conditions & References 4.3. Reductive dehalogenation of halogenated carboxylic acids 2a-c. General procedure General procedure: To 10 mL of a 0.24 M solution of a diorganometal 1 (2.4 mmol), chilled at 0 °C, was added a solution of the appropriate carboxylic acid 2 (1.2 mmol) dissolved in 5 mL of dry THF. The mixture was vigorously stirred and allowed to reach rt over 12 h, after which time it was quenched by slow dropwise addition of H2O (15 mL).

The organic solvent was evaporated in vacuo and the resulting mixture was extracted with CH2Cl2 (3.x.10 mL). The aqueous phase was acidified with 1 N HCl, extracted with CH2Cl2 (3.x.10 mL), and the organic phases were collected, washed with H2O (1.x.10 mL), brine (10 mL), and dried (Na2SO4). After evaporation of the solvent, the resulting mixture was analyzed by 1H NMR. Quenching with D2O was performed by adding 0.75 mL of D2O to the reaction mixture, followed by aqueous work up as described above. Reaction products were characterized by comparison with commercially available samples.

Stage 1: With 1,1,2,2-tetraphenyl-ethanediyl disodium in tetrahydrofuran, Time= 12h, T= 0 - 20 °C , Inert atmosphere

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/96

2016-04-10 14:47:02

Stage 2: With water-d2 in tetrahydrofuran, T= 20 °C , Inert atmosphere Stage 3: With hydrogenchloride in water, regioselective reaction Azzena, Ugo; Dettori, Giovanna; Pisano, Luisa; Pittalis, Mario; Tetrahedron; vol. 67; nb. 19; (2011); p. 3470 3475 View in Reaxys

O

HO

Na +

O–

O

Rx-ID: 1623771 View in Reaxys 11/325 Yield

Conditions & References With sodium methylsulfinylmethanide in dimethyl sulfoxide Lambert,J.B.; Wharry,S.M.; Journal of the American Chemical Society; vol. 104; (1982); p. 5857 View in Reaxys With sodium hydroxide in water Brittain, Harry G.; Crystal Growth and Design; vol. 10; nb. 4; (2010); p. 1990 - 2003 View in Reaxys With sodium hydroxide in water, pH= 8.0 Cui, Xiaoneng; Zhao, Jianzhang; Yang, Pei; Sun, Jifu; Chemical Communications; vol. 49; nb. 87; (2013); p.

10221 - 10223 View in Reaxys 2.1.1 General procedure for preparation of compounds 1a-1k An appropriately substituted phenylacetic acid (40 mmol) was dissolved in 0.1 M NaOH with pH in the range of 9.0 to 10.0. Then, the solvent was removed under reduced pressure to give the corresponding sodium phenylacetate. To a solution of the resulted sodium phenylacetate (40 mmol) in DMSO (45 mL) was added 1.1 equiv of ethyl bromoacetate, which was stirred at 25 °C for 3–4 h. The mixture was then poured into ice-water (50 mL), and extracted twice with 200 mL of EtOAc. The organic layer was dried over MgSO4 followed by removal of the solvent under reduced pressure. The residue was then purified by column chromatography on silica gel to give 1a–1k in yields of 90–95 percent.

With sodium hydroxide in water, pH= 9 - 10 Wang, Xu-Dong; Wei, Wei; Wang, Peng-Fei; Tang, Yun-Tao; Deng, Rui-Cheng; Li, Biao; Zhou, Sha-Sha; Zhang, Jing-Wen; Zhang, Lei; Xiao, Zhu-Ping; Ouyang, Hui; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 22; nb. 14; (2014); p. 3620 - 3628 View in Reaxys

O–

2H

2 Na + H

O

O OH

O O–

Rx-ID: 8623295 View in Reaxys 12/325 Yield 89 %

Conditions & References With arylmalonate decarboxylase (E(1)C4176), water-d2 in various solvent(s), Time= 0.5h, T= 35 °C , pH= 8.5, Decarboxylation, Deuteration Matoishi; Hanzawa; Kakidani; Suzuki; Sugai; Ohta; Chemical Communications; nb. 16; (2000); p. 1519 - 1520 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

7/96

2016-04-10 14:47:02

O

2 Na +

O–

2H

OH

2H –O

O

O

Rx-ID: 8654393 View in Reaxys 13/325 Yield

Conditions & References

92 %

With arylmalonate decarboxylase (E(1)C4176) in various solvent(s), Time= 0.5h, T= 35 °C , pH= 8.5, Decarboxylation Matoishi; Hanzawa; Kakidani; Suzuki; Sugai; Ohta; Chemical Communications; nb. 16; (2000); p. 1519 - 1520 View in Reaxys Cl

Cl

2

H

HO

2H

OH O

HO

O

O

Rx-ID: 30764683 View in Reaxys 14/325 Yield

Conditions & References 4.3. Reductive dehalogenation of halogenated carboxylic acids 2a-c. General procedure General procedure: To 10 mL of a 0.24 M solution of a diorganometal 1 (2.4 mmol), chilled at 0 °C, was added a solution of the appropriate carboxylic acid 2 (1.2 mmol) dissolved in 5 mL of dry THF. The mixture was vigorously stirred and allowed to reach rt over 12 h, after which time it was quenched by slow dropwise addition of H2O (15 mL).

The organic solvent was evaporated in vacuo and the resulting mixture was extracted with CH2Cl2 (3.x.10 mL). The aqueous phase was acidified with 1 N HCl, extracted with CH2Cl2 (3.x.10 mL), and the organic phases were collected, washed with H2O (1.x.10 mL), brine (10 mL), and dried (Na2SO4). After evaporation of the solvent, the resulting mixture was analyzed by 1H NMR. Quenching with D2O was performed by adding 0.75 mL of D2O to the reaction mixture, followed by aqueous work up as described above. Reaction products were characterized by comparison with commercially available samples.

Stage 1: With 1,2-disodiostilbene in tetrahydrofuran, Time= 12h, T= 0 - 20 °C , Inert atmosphere Stage 2: With water-d2 in tetrahydrofuran, T= 20 °C , Inert atmosphere Stage 3: With hydrogenchloride in water, regioselective reaction Azzena, Ugo; Dettori, Giovanna; Pisano, Luisa; Pittalis, Mario; Tetrahedron; vol. 67; nb. 19; (2011); p. 3470 3475 View in Reaxys Br

Br

2H

HO

2H

OH O

O

HO O

Rx-ID: 30764684 View in Reaxys 15/325 Yield

Conditions & References 4.3. Reductive dehalogenation of halogenated carboxylic acids 2a-c. General procedure General procedure: To 10 mL of a 0.24 M solution of a diorganometal 1 (2.4 mmol), chilled at 0 °C, was added a solution of the appropriate carboxylic acid 2 (1.2 mmol) dissolved in 5 mL of dry THF. The mixture was vigorously stirred and allowed to reach rt over 12 h, after which time it was quenched by slow dropwise addition of H2O (15 mL).

The organic solvent was evaporated in vacuo and the resulting mixture was extracted with CH2Cl2 (3.x.10 mL). The aqueous phase was acidified with 1 N HCl, extracted with CH2Cl2 (3.x.10 mL), and the organic phases were collected, washed with H2O (1.x.10 mL), brine (10 mL), and dried (Na2SO4). After evaporation of the solvent, the resulting mixture was analyzed by 1H NMR. Quenching with D2O was performed by adding 0.75 mL of D2O to the reaction mixture, followed by aqueous work up as described above. Reaction products were characterized by comparison with commercially available samples.

Stage 1: With 1,2-disodiostilbene in tetrahydrofuran, Time= 12h, T= 0 - 20 °C , Inert atmosphere Stage 2: With water-d2 in tetrahydrofuran, T= 20 °C , Inert atmosphere Stage 3: With hydrogenchloride in water, regioselective reaction

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/96

2016-04-10 14:47:02

Azzena, Ugo; Dettori, Giovanna; Pisano, Luisa; Pittalis, Mario; Tetrahedron; vol. 67; nb. 19; (2011); p. 3470 3475 View in Reaxys HN

O NH HO HO

O

H N

+H

O

N 3

O–

O–

O

O–

O

O

2 Na +

Rx-ID: 24803391 View in Reaxys 16/325 Yield

Conditions & References 6 : Phenyl-acetate-4-(2-carboxy-ethyl)-3-carboxymethyl-1H-pyrrol-2-ylmethyl-ammonium (9): Example 6 Phenyl-acetate-4-(2-carboxy-ethyl)-3-carboxymethyl-1H-pyrrol-2-ylmethyl-ammonium (9): The solution of 3-[4-Carboxymethyl-5-(phenylacetylamino-methyl)-1H-pyrrol-3-yl]-propionic acid di-lithium salt (8) in 15 ml of a mixture MeOH / H2O (1:1), was diluted with 18 ml H2O and the pH adjusted to 8 with 0.1 N HCI. A suspension of 420 mg (88 UI) of penicillin G acylase in 25 ml H2O was added and the resulting mixture was stirred at R.T. for 20 h.

The beads of enzyme were then filtered off and the crude residue frozen dried.

1H-NMR (400 MHz, CD OD, 298 K): 7.33-7.22 (m, 4H, H aromat. PhAcO-), 7.19-7.15 (m, 1H, H aromat. PhAcO-), 3 6.53 (s, 1H, H-C(5)), 3.99 (s, 2H, H2-C(21)), 3.49 (s, 2H, H2C PhAcO-), 3.37 (s, 2H, H2-C(31)), 2.75 (tripletoΝd, 3J(41, 42).approx.7.8, H2-C(41)), 2.40 (tripletoΝd, 3J(42, 41).approx.7.9, H2-C(42)) 13C-NMR

(100 MHz, CD3OD, 298 K): 181.6 (C(43)), 180.1 (C(32)), 179.4 (C=O PhAcO-), 138.3 (C quaternary aro-

mat. PhAcO-), 129.2, 128.1, 125.9 (C aromat. PhAcO-), 123.3 (C(4)), 120.8 (C(2)), 118.1 (C(3)), 115.3 (C(5)), 45.4 (CH2PhAcO-), 39.1(C(42)), 34.8 (C(21)), 33.8 (C(31)), 22.3 (C(41)) MS ESI(-): [M]-=225.2 With penicillin G acylase in water, Time= 20h, T= 20 °C Patent; Neier, Reinhard; EP1357110; (2003); (A1) English View in Reaxys

H H

OH HO O

N H

H

O O

O

O

OH

S

H

HO

HO

H

O

O HO

O

O O

HO

OH

HO

OH OH

HN H

HO

O

O

H

OHHO O

HO O

OH HO O

HO

H

O

H

H

O O

OH OH

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

9/96

2016-04-10 14:47:02

HN H HO

HO

HO OH O

O

HO

O

H

HO

H

O

O

H

H

O O

OH O

OH HO

OH

Rx-ID: 23048139 View in Reaxys 17/325 Yield

Conditions & References Precipitation of Phenylacetate Salts A mixture of solasonine and solamargine (in an approximately 1:1 ratio) (1.0 g) was dissolved in 10 mL of 3percent acetic acid. Phenylacetic acid (0.255 g) was dissolved in 0.5M ammonium hydroxide (3.75 mL) and added dropwise to the solution. The mixture was left at 4° C. overnight to give a settled fine white powder. The suspension was centrifuged to give a solid and supernatant. On analysis the solid composition contained solasonine:solamargine salts in the ratio 63:37. The supernatant composition of solasonine:solamargine was 34:66.

With ammonia in water, acetic acid, T= 4 °C Patent; SOLBEC PHARMACEUTICALS LTD.; US2004/30109; (2004); (A1) English View in Reaxys

Cu 2+ 3 H O

HO O

2

O

N+

H N

N

N N

O–

O

N

N

O–

N N

6 O–

3 Cu 2+

Rx-ID: 36588710 View in Reaxys 18/325 Yield

Conditions & References

63 %

[Cu3(pa)6(μ3-hmt)]n (2) A methanolic solution (10ml) of Cu(NO3)2·3H2O (0.1208g, 0.5mmol) and phenylacetic acid (0.068g, 0.5mmol) was carefully layered over an aqueous solution (5ml) of hmt (0.140g, 1mmol). A blue crystalline product started to appear within few hours. The compound was collected after two weeks; some of the crystals were suitable for X-ray diffraction analysis. Yield: 0.1198g (63percent). [Yield is calculated with respect to Cu(NO3)2·3H2O]. Anal. Calc. for C54H54Cu3N4O12 (1141.63): C, 56.81; H, 4.77; N, 4.91. Found: C, 56.84; H, 4.73; N, 4.93percent. Selected IR peaks (cm−1): 1622, 1495, 1405, 1293, 1235, 1141, 1013, 939, 812 (see Fig. S1). in methanol, water Hazra, Shantanu; Naiya, Subrata; Sarkar, Biswarup; Drew, Michael G.B.; Ghosh, Ashutosh; Polyhedron; vol.

65; (2013); p. 193 - 199 View in Reaxys

HO N 13C

K

13C

Br

O

Rx-ID: 9321081 View in Reaxys 19/325 Yield 90 %

Conditions & References Stage 1: in ethanol, Time= 29h, T= 25 - 50 °C Stage 2: With sodium hydroxide, Time= 24h, Heating Makosza, Mieczyslaw; Chesnokov, Alexey A.; Tetrahedron; vol. 59; nb. 11; (2003); p. 1995 - 2000 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/96

2016-04-10 14:47:02

HO

H

O

NH 2

HO

O

NH 2Cl

H

O H 2N

OH

O

NH 2

OH

Rx-ID: 29794084 View in Reaxys 20/325 Yield

Conditions & References

100 %

9 :1 part L-ornithine hydrochloride by mole was dissolved in about 4.1 parts water. Subsequently, about 0.5 part calcium hydroxide by mole was added to the solution and stirred for about 30 minutes. The free L-ornithine base was then not isolated by filtration. Next, about 1 part phenyl acetic acid in isopropanol was intermixed with the aqueous Lornithine solution. The final product precipitated from solution was isolated, washed, and dried. Yield: >100percent.

Stage 1: With portlandite in water, Time= 0.5h Stage 2: in water, Product distribution / selectivity Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith, H.; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2012/48043; (2012); (A1) English View in Reaxys 12 :Example 12: Process for Producing L-Ornithine Phenyl Acetate via an Acetate Intermediate[0268] Dissolve 25 mg of L-ornithine HCl 5 vols of H2O, and then add excess acetic acid (about 5 vols) to form a slurry. Subject the slurry to temperature cycling between 25° and 40° C every 4 hours for about 3 days. Add 1 equivalent of phenylacetic acid (with respect to L-ornithine) and stir for about 4-6 hrs (possibly heat). Use IPA as an anti-solvent, add enough to obtain a ratio of 70:30 (IPA:H2O). Isolate by vacuum filtration and dry for about 4-8 hrs at 80 0C to remove any residual acetic acid.

Stage 1: With acetic acid in water, Time= 72h, T= 25 - 40 °C Stage 2: in water, isopropyl alcohol Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2010/115055; (2010); (A1) English View in Reaxys

H

13C 2

N

H

13C 2

HO O

Rx-ID: 2535391 View in Reaxys 21/325 Yield

Conditions & References

90.4 %

With potassium hydroxide, ethanol, water Apeloig, Yitzhak; Franke, Wilfried; Rappoport, Zvi; Schwarz, Helmut; Stahl, Daniel; Journal of the American Chemical Society; vol. 103; nb. 10; (1981); p. 2770 - 2780 View in Reaxys

O

O O

O–

K+

Rx-ID: 29893497 View in Reaxys 22/325 Yield 95 %

Conditions & References With potassium tert-butylate, water in ethanol, T= 60 °C Shang, Rui; Yang, Zhi-Wei; Wang, Yan; Zhang, Song-Lin; Liu, Lei; Journal of the American Chemical Society; vol. 132; nb. 41; (2010); p. 14391 - 14393 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

11/96

2016-04-10 14:47:02

H N

OH

H N

O

O

O

HO

O

NH O

O

NH 2

O

O OH NH 2

N H

O

H N

N H

O

H N

O OH

O

Rx-ID: 41863816 View in Reaxys 23/325 Yield

Conditions & References 1.P : Phenylacetic Acid-Ile-Lys-Val-Ala-Val (Benzyl-IKVAV) Synthesis Then, the C-terminal of the resin in anhydrous DMF and DIEA (0.83 mL, 5 mmol) was loaded with Fmoc-valine-OH (0.678 g, 2 mmol) for 1 hour.

During the deprotection of Fmoc groups, 20percent of piperidine in a DMF solution was used for 20 minutes, and then repeated twice (2 minutes for each time).

Subsequently, Fmoc-alanine-OH (0.623 g, 2 mmol) was coupled to free amino for 40 minutes by using HBTU (0.758 g, 2 mmol) and DIEA (0.83 mL, 5 mmol) as coupling agents.

After that, during the deprotection of Fmoc groups, 20percent of piperidine in a DMF solution was used for 20 minutes, and then repeated twice (2 minutes for each time).

After that, Fmoc-valine-OH (0.678 g, 2 mmol) was coupled to free amino for 40 minutes by using HBTU (0.758 g, 2 mmol) and DIEA (0.83 mL, 5 mmol) as coupling agents.

During the deprotection of Fmoc groups, 20percent of piperidine in a DMF solution was used for 20 minutes, and then repeated twice (2 minutes for each time).

Subsequently, as described in the above steps, Fmoc-lysine(Boc)-OH (0.937 g, 2 mmol) and Fmoc-isoleucine-OH (0.707 g, 2 mmol) were coupled to free amino for 40 minutes by using HBTU (0.758 g, 2 mmol) and DIEA (0.83 mL, 5 mmol) as coupling agents.

After that, during the deprotection of Fmoc groups, 20percent of piperidine in a DMF solution was used for 20 minutes, and then repeated twice (2 minutes for each time).

Finally, phenylacetic acid (0.45 g, 3 mmol) was coupled to free amino by using HBTU (1.1 g, 3 mmol) and DIEA (1.25 mL, 7.5 mmol) as coupling agents.

The reaction mixture was stirred overnight and the excess reagent was removed by DMF, DCM, MeOH and hexane.

The peptide derivative was cut off for 3 hours by using a 90percent solution of trifluoroacetic acid in deionized water.

The obtained solution was dried with air and was precipitated by adding ether to obtain the target product.

The solid was vacuum dried to remove the remaining solution (white solid: 0.46 g).

1H NMR (300 MHz, DMSO-d6): δ=0.8-2.2 (m, 32H), 2.766 (m, 2H), 2.85-3.15 (m, 2H), 4.10-4.50 (m, 5H), 7.15-7.40 (m, 5H), 7.6-8.25 (m, 7H); 13C NMR (75 MHz, DMSO-d6): δ=11.9, 16.3, 18.8, 19.1, 20.0, 20.1, 22.6, 23.2, 25.3, 27.5, 30.7, 30.9, 31.7, 32.1, 37.6, 43.0, 44.7, 48.9, 53.4, 57.9, 58.0, 58.2, 127.2, 129.1, 129.9, 137.6, 171.2, 171.3, 172.1, 172.3, 173.0, 173.2, 173.8, 171.7; MS (EST+): calculated 660.4; measured 661.5 (M-H)+.

With trifluoroacetic acid in water, DMFA Patent; National Chiao Tung University; Lin, Hsin-Chieh; Hsu, Shu-Min; (42 pag.); US2016/9763; (2016); (A1) English View in Reaxys

2H

O

O

2H

Cl

2H 2

H

HO

O

Rx-ID: 2000450 View in Reaxys 24/325 Yield 65 %

Conditions & References With magnesium in diethyl ether, T= -30 °C Heesing, Albert; Muellers, Wolfgang; Chemische Berichte; vol. 113; nb. 1; (1980); p. 9 - 18

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

12/96

2016-04-10 14:47:02

View in Reaxys 2H

2H

2H

2H

HO

O

N

Rx-ID: 5144773 View in Reaxys 25/325 Yield

Conditions & References

74 %

With NaOD, tetrabutylammomium bromide in water-d2, Time= 5h, Heating Kim, Sung Soo; Tuchkin, Alexey; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3821 - 3824 View in Reaxys

O HO

C

O

Na +

O–

O

Cl

Rx-ID: 11217628 View in Reaxys 26/325 Yield

Conditions & References

97 %

With sodium hydroxide, dicobalt octacarbonyl, T= 60 - 65 °C , p= 760.051 - 2280.15Torr Zhesko; Boyarskii; Nikitina; Russian Journal of Applied Chemistry; vol. 80; nb. 6; (2007); p. 945 - 950 View in Reaxys

OH O

O

HO

HO

O

H

O

HO

OH

HO

O

HN

H

O OH

O

H H

H O

OH OH

Rx-ID: 23147219 View in Reaxys 27/325 Yield

Conditions & References 2 : Precipitation of [PHENYLACETATE] salts A mixture of solasonine and solamargine (in an approximately 1: 1 ratio) (1.0 g) was dissolved in 10 mL of 3percent acetic acid. [PHENYLACETIC] acid (0.255 g) was dissolved in 0.5M ammonium hydroxide (3.75 mL) and added dropwise to the solution. The mixture was left at [4°C] overnight to give a settled fine white powder. The suspension was centrifuged to give a solid and supernatant. On analysis the solid composition contained solasonine : solamargine salts in the ratio 63: 37. The supernatant composition of solasonine : solamargine was 34: 66.

With ammonia, acetic acid in water Patent; SOLBEC PHARMACEUTICALS LIMITED; WO2004/2998; (2004); (A1) English View in Reaxys

O

4

2 OH – O–

O

2

N

OH

N Ni 2+

4H O 2

4H O 2

4 Ni 2+

O–

2 OH

OH

O–

N OH

N

HO

Rx-ID: 36932816 View in Reaxys 28/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

13/96

2016-04-10 14:47:02

Yield 71 %

Conditions & References With triethylamine in methanol, Time= 2.5h, T= 20 °C Ghosh, Aloke Kumar; Shatruk, Michael; Bertolasi, Valerio; Pramanik, Kausikisankar; Ray, Debashis; Inorganic Chemistry; vol. 52; nb. 24; (2013); p. 13894 - 13903 View in Reaxys H C–

O

HO O

2 Li+

O–

Rx-ID: 1623789 View in Reaxys 29/325 Yield

Conditions & References With n-butyllithium in tetrahydrofuran, T= -78 °C , further acids and lithiating agents Renaud, Philippe; Fox, Marye Anne; Journal of the American Chemical Society; vol. 110; nb. 17; (1988); p. 5705 5709 View in Reaxys With naphthalene, lithium in tetrahydrofuran, Time= 2h, Ambient temperature Mladenova, M.; Blagoev, B.; Gaudemar, M.; Gaudemar-Bardone, F.; Lallemand, J. Y.; Tetrahedron; vol. 37; (1981); p. 2157 - 2164 View in Reaxys With methyllithium in tetrahydrofuran Lambert,J.B.; Wharry,S.M.; Journal of the American Chemical Society; vol. 104; (1982); p. 5857 View in Reaxys With n-butyllithium, diethylamine in tetrahydrofuran, Time= 2h, Ambient temperature Brun, Eva M.; Gil, Salvador; Mestres, Ramon; Parra, Margarita; Villar, Felix; Tetrahedron Letters; vol. 39; nb. 9; (1998); p. 1055 - 1058 View in Reaxys

F

etheric <α14C>benzyl magnesium chloride

B

F

F

HO O

Rx-ID: 8220783 View in Reaxys 30/325 Yield

Conditions & References With carbon dioxide, chloro(phenylmethyl)-magnesium, T= -5 °C , Herstellung von Phenyl-<2-14C>essigsaeure enthaltender Phenylessigsaeure Dauben; Coad; Journal of the American Chemical Society; vol. 71; (1949); p. 2928 View in Reaxys 2H

2H

O

HO O

HO

Rx-ID: 10119615 View in Reaxys 31/325 Yield 34 %, 10 %

Conditions & References With Oxonereg;, (ethylenedinitrilo)tetraacetic acid disodium salt, sodium hydrogencarbonate in acetone, acetonitrile, Time= 15h, T= 10 °C Zeller, Klaus-Peter; Kowallik, Meike; Haiss, Peter; Organic and Biomolecular Chemistry; vol. 3; nb. 12; (2005); p.

2310 - 2318 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

14/96

2016-04-10 14:47:02

N O Co

O

6 2+ H 2O

HO

O 2

N

O–

N

N

O

O N

HO

N

O

O– N

2

N

O 2H O 2

Co 2+

N

Rx-ID: 38578670 View in Reaxys 32/325 Yield

Conditions & References

70 %

With sodium hydroxide in water, Time= 72h, T= 100 °C , pH= Ca. 6, Autoclave Guo, Wei; Han, Li-Qiang; Guo, Ya-Mei; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 539 - 547 View in Reaxys N O

6 H

O

H2

O

N+

O

O–

HO N

O–

N

O

O N

HO

N

Ni 2+

O– N

2

N

O 2H O 2

Ni 2+

N

Rx-ID: 38578672 View in Reaxys 33/325 Yield

Conditions & References

66 %

With sodium hydroxide in water, Time= 72h, T= 100 °C , pH= Ca. 6, Autoclave Guo, Wei; Han, Li-Qiang; Guo, Ya-Mei; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 539 - 547 View in Reaxys

O

HO

Li+

O–

O

Rx-ID: 1623791 View in Reaxys 34/325 Yield

Conditions & References With methyllithium in tetrahydrofuran Lambert,J.B.; Wharry,S.M.; Journal of the American Chemical Society; vol. 104; (1982); p. 5857 View in Reaxys

HO

H N

N N

OH

HO

Cl

N

H O

O O

N H

N

O O

Rx-ID: 19769322 View in Reaxys 35/325 Yield

Conditions & References Reaction Steps: 2 1: 58 percent / triethylamine / dimethylformamide 2: H2O; CHCl3 With triethylamine in chloroform, water, N,N-dimethyl-formamide Echavarren, Antonio; Galan, Amalia; Lehn, Jean-Marie; Mendoza, Javier de; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4994 - 4995 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

15/96

2016-04-10 14:47:02

HO

Cl

N O

O

O

N H

O

O

N

O

Rx-ID: 19792283 View in Reaxys 36/325 Yield

Conditions & References Reaction Steps: 2 1: 58 percent / triethylamine / dimethylformamide 2: H2O; CHCl3 With triethylamine in chloroform, water, N,N-dimethyl-formamide Echavarren, Antonio; Galan, Amalia; Lehn, Jean-Marie; Mendoza, Javier de; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4994 - 4995 View in Reaxys H

13C 2

HO

H 13 2 C

O

Br

Rx-ID: 20537294 View in Reaxys 37/325 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / aq. ethanol 2: 90.4 percent / KOH, EtOH, H2O With potassium hydroxide, ethanol, water in ethanol Apeloig, Yitzhak; Franke, Wilfried; Rappoport, Zvi; Schwarz, Helmut; Stahl, Daniel; Journal of the American Chemical Society; vol. 103; nb. 10; (1981); p. 2770 - 2780 View in Reaxys

O OH 2

P

P

2

O– O

O

Cu +

O–

Cu +

Rx-ID: 26952524 View in Reaxys 38/325 Yield 83.8 %

Conditions & References in tetrahydrofuran, Kinetics, byproducts: CO2; Ar- or CO2-atmosphere; addn. of solvent to Cu-complex, heating (55.4°C, 10 min, IR monitoring); cooling to room temp., crystn. (overnight); elem. anal.

Darensbourg, Donald J.; Holtcamp, Matthew W.; Khandelwal, Bandana; Reibenspies, Joseph H.; Inorganic Chemistry; vol. 33; (1994); p. 531 - 537 ; (from Gmelin) View in Reaxys in tetrahydrofuran, Kinetics, byproducts: CO2; inert atmosphere, 55.4 °C Darensbourg, Donald J.; Holtcamp, Matthew W.; Khandelwal, Bandana; Klausmeyer, Kevin K.; Reibenspies, Joseph H.; Inorganic Chemistry; vol. 34; (1995); p. 2389 - 2398 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

16/96

2016-04-10 14:47:02

10 Cu 2+

6

O–

5

HO

–O

O–

5 Cu 2+

N

O H

H 2N H

O

O

H

2 Gd 3+

16

O

O 3

Gd 3+

N

H

O–

10

O

O–

H

O–

N H 2N H

Rx-ID: 28726452 View in Reaxys 39/325 Yield

Conditions & References

68 %

With NaOH in water, aq. soln. of NaOH added to aq. soln. of phenylacetic acid; dried; dissolved in H2O; added to soln. of Gd-Cu complex in H2O; MeOH added until complex completely dissolved; crystd. by slow evapn.; elem. anal.

Lim, Choong-Sun; Kampf, Jeff W.; Pecoraro, Vincent L.; Inorganic Chemistry; vol. 48; nb. 12; (2009); p. 5224 5233 ; (from Gmelin) View in Reaxys

O

O

HO H 2N

O

O OH

OH NH 2

O H 2N

OH OH

NH 2

Rx-ID: 33014872 View in Reaxys 40/325 Yield

Conditions & References

53.5 %

3 :Phenyl acetic acid (PAA) was dissolved in a solution of isopropanol. About 1 molar equivalent of sodium hydroxide was added to the solution and stirred. The obtained solution was added dropwise to a solution having about 1 molar equivalent of L- ornithine benzoate. L-ornithine phenyl acetate was precipitated from this solution using generally the same procedures described in Example 2. Yield: 53.5percent. The white powder was further characterized and is summarized in TABLE 6 under the heading "Trial A." Stage 1: With sodium hydroxide in isopropyl alcohol Stage 2: in isopropyl alcohol, Product distribution / selectivity Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith, H.; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2012/48043; (2012); (A1) English View in Reaxys

O 13C

O

NH

13C

O

N H

Na + O–

Rx-ID: 36973206 View in Reaxys 41/325 Yield

Conditions & References

90 %

With sodium hydroxide, Time= 5h, T= 100 °C Lichtenecker, Roman J.; Weinhaeupl, Katharina; Schmid, Walther; Konrat, Robert; Journal of Biomolecular NMR; vol. 57; nb. 4; (2013); p. 327 - 331 View in Reaxys N O

6 H

O

H2

Zn 2+

O

N+ O–

O

O–

HO N

O– N

2

N

O

O N

HO

N

N

O 2H O 2

Zn 2+

N

Rx-ID: 38578671 View in Reaxys 42/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

17/96

2016-04-10 14:47:02

Yield

Conditions & References

63 %

With sodium hydroxide in water, Time= 72h, T= 100 °C , pH= Ca. 6, Autoclave Guo, Wei; Han, Li-Qiang; Guo, Ya-Mei; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 539 - 547 View in Reaxys

H 18O

HO

18O

O

Rx-ID: 9936700 View in Reaxys 43/325 Yield

Conditions & References With sulfuric acid, H2 18O in 1,4-dioxane, T= 75 °C Sorensen-Stowell, Kerensa; Hengge, Alvan C.; Journal of Organic Chemistry; vol. 70; nb. 12; (2005); p. 4805 4809 View in Reaxys

O O

O

Na

O–

Na +

Rx-ID: 25592803 View in Reaxys 44/325 Yield

Conditions & References 4.7 g. of sodium, 30 ml of absolute toluene and 6 mg of catalyst are put into a stainless-steel preliminary reactor that has a mixer capable of mixing at 10,000 revolutions per minute, a heater, a backflow condenser, a viewing window, and a cooling jacket. All processes are carried out in a dry-nitrogen atmosphere. The reactor is heated up to the toluene boiling point Then the high-speed mixer is switched on for 1-1.5 minutes for sodium crushing.The suspension is then cooled down to 25-30° C. and placed in a phenylsodium-conversion reactor. 5-8 ml of a chlorobenzene and toluene solution, made by mixing the 2 reagents in equal proportion with catalyst, is added to toluene-sodium suspension while mixing and cooling the reactor to 2740° C. The reaction begins immediately and black sediments of phenylsodium are generated in the reactor. The temperature of reaction mixture is kept at 2740° C. The chlorobenzene metallizing reaction takes approximately 1 hour.The suspension of phenylsodium is taken from the pheynylsodium-conversion reactor to a reserve tank, where reaction is completed in a nitrogen atmosphere. In order to transform phenylsodium into benzylsodium, the contents of the reserve tank are placed into a benzylsodium-conversion reactor, where the suspension boils for 1-1.5 hours. While boiling, the solution's color gets brick-red and then black again.Upon completion of the reaction, the hot solution is removed from the benzylsodium-conversion reactor and placed into a cooling tank. Then as soon as possible, the cooled reaction mass is poured into crushed dry ice in a carbonation reactor and mixed. When vaporization of the CO2 is completed, 20 ml of water is added to the residue during cooling and mixing. The water layer is then separated and acidulated with hydrochloric acid to a pH around pH 2. The generated sediment phenylacetic acid is separated by filtration in a vacuum-filter. 12.5 g. of phenylacetic acid (92percent) with melting point 77° C. is produced. The results of other experiments are given in the Table 1.

TABLE 1 Experimental results of PhAA production in the absence and presence of catalyst respectively PhAA production in the PhAA yields in the absence of catalyst, percent presence of catalyst, percent Time of Rate of addition of toluene Rate of addition of toluene boiling of solution of chlorobenzene solution of chlorobenzene phenylsodium and toluene suspension of and toluene suspension of in toluene, hr. sodium, 4.3 mole/hr. sodium, 4.3 mole/hr. 2.5 3.5 4.3 5 2.5 3.5 4.3 5 0.5 16.2 18.9 27 33 66 74 75 70 1 34.6 40.5 48 54 83.5 90 94.5 89 2 42.8 44.8 52 58 83.4 89.8 93.7 86.7 3 52.5 60.4 62.5 69 80.8 90.6 90.3 85.9 4 49.6 58.4 66.5 - 76 87 88 80.8 The table shows that including a catalyst greatly increases phenylacetic-acid yield. The highest yield of the product is observed when the time of boiling in toluene equals 1 hour time. Further increase in boiling time causes a decrease in desired product yield.

Also, the application of a catalyst improves the stability of the results.It was also observed that the increase in catalyst amount to 0.001percent leads to a rise in yield of the desired product. Further increases in catalyst amount do not generally give an increase of the desired product in toluene Patent; Property Development Corporation International, Ltd, Inc.; US7161026; (2007); (B1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

18/96

2016-04-10 14:47:02

4

H O

HO

O

N

4 O

H

O Zr 4+

O–

(v2) – 2 O O

2+Zr

O

C H2

Rx-ID: 26640936 View in Reaxys 45/325 Yield 87 %

Conditions & References With NaOH in water, Addn. of NaOH dissolved in distd. H2O to org. compd. and stirring. Addn. of Zr(NO3)4 in distd.

H2O to the acidic filtered soln. and stirring of mixt.; Immediate pptn. of solid, filtn., washing with H2O, drying in desiccator and then in vac. over P4O10 at 50°C for 5 h, elem. anal.

Ikekwere, P. O.; Daramola, O. Y.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 19; (1989); p. 699 - 714 ; (from Gmelin) View in Reaxys

HO O

N

N

O OH

Rx-ID: 28308195 View in Reaxys 46/325 Yield

Conditions & References 8 :8. N,N-Dimethylethylammonium phenylacetate;N,N-Dimethylethylamine (l.Omol, 73.14g) was placed in an argonflushed round- bottomed flask equipped with a magnetic stirrer and cooled to 0°C in an ice bath. Phenylacetic acid (1.00 equiv., l.Omol, 136.15g) was added portionwise with stirring at such a rate as to prevent the temperature of the reaction form exceeding 4O0C. After the addition of the last of the acid, the reaction was stirred on ice for 25 minutes. The resultant product was a colourless liquid with the following properties:Viscosity (at) 250C: 17.7cP <n="17"/ >Density (at) 25°C: 1.00 g/cm3 Refractive Index (at) 25 °C: 1.499 π*: 0.85 β: 0.95; , Time= 0.416667h, T= 0 - 40 °C Patent; BIONIQS LIMITED; WO2009/34329; (2009); (A1) English View in Reaxys

HO O

N N

O OH

Rx-ID: 28308196 View in Reaxys 47/325 Yield

Conditions & References 17 :17. N,N-Dimethylbutylammonium phenylacetate; N,N-Dimethylbutylamine (l.Omol, 101.19g) was placed in an argon-flushed round- bottomed flask equipped with a magnetic stirrer and cooled to 00C in an ice bath. Phenylacetic acid (1.00 equiv., l.Omol, 136.15g) was added portionwise with stirring at such a rate as to prevent the temperature of the reaction form exceeding 40°C. After the addition of the last of the acid, the reaction was stirred on ice for 25 minutes. The resultant product was a colourless liquid with the following properties: <n="23"/>Viscosity (at) 25°C: 15.OcPDensity (at) 25°C: 0. 96 g/cm3Refractive Index (at) 25°C: 1.488 π*: 0.78 α: 1.20 β: 0.97EN T: 0.85 , Time= 0.416667h, T= 0 - 40 °C Patent; BIONIQS LIMITED; WO2009/34329; (2009); (A1) English View in Reaxys

H 18O N

18O

Rx-ID: 28520544 View in Reaxys 48/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

19/96

2016-04-10 14:47:02

Yield

Conditions & References With hydrogenchloride, H2 18O in tetrahydrofuran, T= 50 °C , Inert atmosphere Sanki, Aditya K.; Talan, Rommel S.; Sucheck, Steven J.; Journal of Organic Chemistry; vol. 74; nb. 5; (2009); p.

1886 - 1896 View in Reaxys

HO

O

(v2)

Zn

O

Zn

(v1)

OH

Rx-ID: 41220668 View in Reaxys 49/325 Yield

Conditions & References

89%

in tetrahydrofuran, hexane, Time= 1h, T= -78 - 20 °C , Inert atmosphere, Schlenk technique Grala, Agnieszka; Wolska-Pietkiewicz, Malgorzata; Wojewdzka, Anna; Dabergut, Monika; Justyniak, Iwona; Lewiski, Janusz; Organometallics; vol. 34; nb. 20; (2015); p. 4959 - 4964 View in Reaxys 2H

2H

O

O

2H

Br 2H

2H

HO O

2H

2H

2H

2H 2H

Rx-ID: 29256375 View in Reaxys 50/325 Yield 46 %

Conditions & References Stage 1: With magnesium in diethyl ether Stage 2: in diethyl ether, Time= 0.5h Thiel, Verena; Brinkhoff, Thorsten; Dickschat, Jeroen S.; Wickel, Susanne; Grunenberg, Joerg; Wagner-Doebler, Irene; Simon, Meinhard; Schulz, Stefan; Organic and Biomolecular Chemistry; vol. 8; nb. 1; (2010); p. 234 246 View in Reaxys

O

O H 2N

OH

O OH

O

O–

Na +

NH 2

O H 2N

OH NH 2

OH

Rx-ID: 29794085 View in Reaxys 51/325 Yield 57 %

Conditions & References 4 :Example 4: Small-scale Batch Process to Produce L-Ornithine Phenyl Acetate [0248] About 8.4g (0.049moles) of L-ornithine HCl was dissolved in 42 mL H2O and, separately, about 11.4g of silver benzoate was dissolved in 57mL DMSO. Subsequently, the silver benzoate solution was added to the L-ornithine HCl solution. Combining the two mixtures resulted in an immediate, exothermic precipitation of a creamy white solid (AgCl). The solid was removed by vacuum filtration and retaining the filtrate (L-ornithine benzoate in solution). 20OmL of IPA was added to the filtrate and the mixture was cooled to 4°C. A crystalline solid precipitated after about 3 hours (L- ornithine benzoate) which was isolated by vacuum filtration. Yield: 60 percent[0249] 7.6 g (0.03moles) of the L-ornithine benzoate was dissolved in 38 mL H2O and about 4.4g of sodium phenyl acetate was dissolved 22 mL H2O. Subsequently, the sodium phenyl acetate solution was added to the L-ornithine benzoate solution and left to stir for about 10 minutes About 24OmL of IPA (8:2 IPA:H2O) was added and the solution stirred for 30 minutes before cooling to 4°C. A crystalline solid precipitated after about 3 hrs at 4°C (L-ornithine phenyl acetate). The precipitate was isolated by vacuum filtration and washed with 48-144mL of IPA. Yield: 57 percent in water, isopropyl alcohol, Time= 0.666667h Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2010/115055; (2010); (A1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

20/96

2016-04-10 14:47:02

2 :About 75 kg of L-Ornithine monohydrochloride was dissolved in 227 kg of water. To the resulting solution was added 102 kg of silver benzoate dissolved in 266 kg of DMSO at room temperature within 2 hours. Initially, a strong exothermy was observed and the silver chloride precipitated. The receiver containing the solution was then washed with 14 kg of DMSO that was added to the reaction mass. In order to remove the silver chloride formed, the reaction mass was filtered over a lens filter prepared with 10 kg of Celite and a GAF filter of 1 mm. After filtration, the filter was washed with an additional 75 kg of water. The reaction mass was placed in a different tank after filtration to prevent contamination with residual silver chloride. The reaction mass was then heated at 35 + 2 °C and 80 kg of sodium phenyl acetate was added. At this point the reaction mass was stirred at 35 + 2 °C for at least 30 minutes.

[0158] In order to precipitate the final product, 353 kg of IPA was added to the reaction mass. The reaction mass was then cooled to 0 + 3 °C within 6 hours, stirred for 1 hour and then the product isolated in a centrifuge.[0159] About 86 kg of final wet product was obtained. The product was then dried at 40 + 5 °C for about 6.5 to 8 hours to provide about 75 kg of L-ornithine phenyl acetate. Yield: 63.25percent. in water, dimethyl sulfoxide, Time= 0.5h, T= 33 - 37 °C , Industry scale, Product distribution / selectivity Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith, H.; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2012/48043; (2012); (A1) English View in Reaxys

HO

O

2

Cl O

O

O– 6 H O

EN

Mn2+

O

O–

O–

N

E

OH

EN

2 O–

OH

H

O

NE –O

2 Mn3+

Cl O OO

Rx-ID: 31143660 View in Reaxys 52/325 Yield

Conditions & References

69 %

With N(C2H5)3, air in methanol, soln. of diimine added to soln. of Mn(ClO4)2 with stirring, after ca. 15min soln. of cinnamic acid added, N(C2H5)3 added dropwise with stirring; son. slowly evapd., solids filtered off, washed (diethyl ether); elem. anal.

Kar, Paramita; Guha, Pampa M.; Drew, Michael G. B.; Ishida, Takayuki; Ghosh, Ashutosh; European Journal of Inorganic Chemistry; nb. 13; (2011); p. 2075 - 2085 ; (from Gmelin) View in Reaxys

O

O

13C

Br

HO

Mg

13C

O

Rx-ID: 2192106 View in Reaxys 53/325 Yield 66 %

Conditions & References Apeloig, Yitzhak; Franke, Wilfried; Rappoport, Zvi; Schwarz, Helmut; Stahl, Daniel; Journal of the American Chemical Society; vol. 103; nb. 10; (1981); p. 2770 - 2780 View in Reaxys 2H

2H

2H

HO 2H

2H

O

HO

O2H

2H

Rx-ID: 9060566 View in Reaxys 54/325 Yield

Conditions & References With deuterated Raney alloy in water-d2, T= 100 °C

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

21/96

2016-04-10 14:47:02

Flakus, Henryk T.; Chelmecki, Michal; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 58; nb. 9; (2002); p. 1867 - 1880 View in Reaxys

O–

HO Pd

O

2

O

Pd2+

Rx-ID: 27510822 View in Reaxys 55/325 Yield 72 %

Conditions & References With aq. NaOH in methanol, nitric acid, aq. HNO3; pH 6.5; stoirring (1 h); elem. anal.

Yuqiu, Gong; Liang, Shen; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 26; nb. 9; (1996); p. 1489 - 1496 ; (from Gmelin) View in Reaxys

HO

P

N

Cu

O

N O– O P 3

Cu +

Rx-ID: 28324677 View in Reaxys 56/325 Yield 97 %

Conditions & References With triethylamine in acetonitrile, byproducts: H2; Electrolysis; (Ar); Cu electrodes used; at 4.0 V at 40°C for 4.5 h; evapd. (vac.); obtained as an oil; elem. anal.

Jakob, Alexander; Shen, Yingzhong; Waechtler, Thomas; Schulz, Stefan E.; Gessner, Thomas; Riedel, Ralf; Fasel, Claudia; Lang, Heinrich; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 634; nb. 12-13; (2008); p. 2226 - 2234 ; (from Gmelin) View in Reaxys

N O

N N N

K+ BH–N

N

O O–

Na +

Cl 2Fe

N O–

N

N

BH– N

N

N

Fe 2+

Rx-ID: 39897409 View in Reaxys 57/325 Yield 68 %

Conditions & References Stage 1: in dichloromethane, Time= 1h Stage 2: in methanol, dichloromethane, Time= 8h Sheet, Debobrata; Bhattacharya, Shrabanti; Paine, Tapan Kanti; Chemical Communications (Cambridge, United Kingdom); vol. 51; nb. 36; (2015); p. 7681 - 7684 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

22/96

2016-04-10 14:47:02

O

2H

O

OH

O

O

O

Rx-ID: 15681718 View in Reaxys 58/325 Yield

Conditions & References Reaction Steps: 3 1.1: NaH / tetrahydrofuran / 5 h / Heating 1.2: 96 percent / D2O; DCl 2.1: 90 percent / NaOD; D2O / CH3OD / 12 h / 20 °C 3.1: 92 percent / arylmalonate decarboxylase (E(1)C4176) / various solvent(s) / 0.5 h / 35 °C / pH 8.5 With NaOD, arylmalonate decarboxylase (E(1)C4176), water-d2, sodium hydride in tetrahydrofuran, methanol-d1, 1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Decarboxylation Matoishi; Hanzawa; Kakidani; Suzuki; Sugai; Ohta; Chemical Communications; nb. 16; (2000); p. 1519 - 1520 View in Reaxys

2H

O 2H

O

OH

O

O O

Rx-ID: 15691042 View in Reaxys 59/325 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / NaOD; D2O / CH3OD / 12 h / 20 °C 2: 92 percent / arylmalonate decarboxylase (E(1)C4176) / various solvent(s) / 0.5 h / 35 °C / pH 8.5 With NaOD, arylmalonate decarboxylase (E(1)C4176), water-d2 in methanol-d1, 1: Hydrolysis / 2: Decarboxylation Matoishi; Hanzawa; Kakidani; Suzuki; Sugai; Ohta; Chemical Communications; nb. 16; (2000); p. 1519 - 1520 View in Reaxys O–

2H O 2

HO

H 2N

H

O

O

Cl 2Cu

2

NH 2

Cu 2+ O

H

H 2N 2 NH 2

Rx-ID: 26766299 View in Reaxys 60/325 Yield 70 %

Conditions & References With NH3 in ethanol, water, byproducts: NH4(1+), H2O; neutralising an alcoholic soln. of phenylacetic acid with ammonia, addn. of N2H4*H2O to the ammonium phenylacetate, slow addn. of the metal salt and stirring; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys

HO

2

–O

O

4 H

O

H

O

O– H 2N

H O

NH 2

2

H 2N 2 NH 2 O

H

Mn2+

Mn2+

Rx-ID: 26774115 View in Reaxys 61/325 Yield 70 %

Conditions & References With NH3 in ethanol, water, byproducts: NH4(1+), H2O; neutralising an alcoholic soln. of phenylacetic acid with ammonia, addn. of N2H4*H2O to the ammonium phenylacetate, slow addn. of the metal salt and stirring; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

23/96

2016-04-10 14:47:02

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys Fe 2+ 6 H

HO

O

2 NH + – 4 O 2

O

O–

H H

O–

O

S

O

H 2N

2

NH 2

Fe 2+ O

H

H 2N 2 NH 2

O

Rx-ID: 26786732 View in Reaxys 62/325 Yield

Conditions & References

70 %

With NH3 in ethanol, water, byproducts: NH4(1+), H2O; neutralising an alcoholic soln. of phenylacetic acid with ammonia, addn. of N2H4*H2O to the ammonium phenylacetate, slow addn. of the metal salt and stirring; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys

NH

H

2 N

N

2

O

H N

O

O–

H

O

10 O–

Mn2+

Mn6O2( 10+)

Rx-ID: 33139755 View in Reaxys 63/325 Yield

Conditions & References

73 %

in ethanol, soln. pyrazine in EtOH was added to soln. Mn(PhCH2COO)2*H2O in EtOH, refluxed for 2 h, soln. was cooled and filtered, left to stand for 1-2 daysat room temp., ppt. was dissolved in MeCN and filtered; soln. was evapd. slowly for several days; elem. anal.

Kar, Paramita; Haldar, Ritesh; Gomez-Garcia, Carlos J.; Ghosh, Ashutosh; Inorganic Chemistry; vol. 51; nb. 7; (2012); p. 4265 - 4273 ; (from Gmelin) View in Reaxys

HO

6 H

O

H2

O

O

N+

O–

Zn 2+

O 3

2

–O

O

4 H

O–

O

H

H 2N

H O

Mn2+

H

(v1)

NH 2

-2

O

Fe 2+ (v1)

O

S OO

O– H 2N 2 NH 2

Fe 0.5Mn0.25Zn( 1.5+)

Rx-ID: 39454726 View in Reaxys 64/325 Yield

Conditions & References Preparation of Manganese Zinc Ferrous PhenylacetateHydrazinate Mn0.5Zn0.5Fe2(PhAc)3(N2H4)2 Manganese zinc ferrous phenylacetate hydrazinate was prepared by mixing an aqueous solution containing the requisite quantity of phenylacetic acid and hydrazine hydrate to the solution containing the stoichiometric amount of freshly prepared ferrous sulfate solution mixed with manganese acetate tetrahydrate and zinc nitrate hexahydrate with constant stirring.The complex is precipitated slowly, which is kept for some time. A yellow-colored precipitate thus obtained was filtered off, washed with ethanol, dried with diethyl ether, and then stored in a vacuum desiccator. in water Rangasamy, Sinduja; Kalimuthu, Kalpanadevi; Rakkiyasamy, Manimekalai; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 45; nb. 4; (2015); p. 482 - 486 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

24/96

2016-04-10 14:47:02

2H

O 2H

2H

2

H

O O 2H

O 2

H

O

O

Rx-ID: 2840184 View in Reaxys 65/325 Yield

Conditions & References

85 %

T= 180 °C McCarthy, Daniel G.; Hegarty, Anthony F.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 579 - 591 View in Reaxys

F

1-phenyl-<1-13C>ethanone-(1)

O

B

F

HO

F

O

Rx-ID: 8220782 View in Reaxys 66/325 Yield

Conditions & References With morpholine, sulfur, Erhitzen des Reaktionsprodukts mit wss. Kalilauge; Herstellung von Phenyl-<2-13C>essigsaeure enthaltender Phenylessigsaeure Shantz; Rittenberg; Journal of the American Chemical Society; vol. 68; (1946); p. 2109 View in Reaxys

18

O

N

18O

OH

N

Rx-ID: 9483359 View in Reaxys 67/325 Yield 90 %

Conditions & References in 1,4-dioxane, water, Time= 0.75h, Irradiation Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

(v3)

OH 2

(v3)

H

2H O 2

HO N O

O 6 O–

N

(v4) Cu 2+H N SP-5 O– N (v4) (v5) – (v5)2+ (v4) (v4) N O Cu N SP-5 (v4) (v4) 2+ (v4) – Cu H N SP-5 O N (v4) (v5) H – (v5)2+ (v4) N O Cu N (v4) SP-5 (v4) (v4) Cu 2+O– N SP-5 N (v5)(v3) – (v5)(v4) (v4) N O Cu 2+N (v4) H SP-5 2 (v4) OH 2 (v3)

Cl 2Cu

12

H O

H

Rx-ID: 30051445 View in Reaxys 68/325 Yield 57 %

Conditions & References With Na2CO3 in ethanol, water, 1 M soln. Na2CO3 was added to aq. soln. CuCl2*2H2O, ppt. was centrifugated, washed with water, transferred in aq. EtOH, 2,2'-bipyridine and phenylacetic acid in aq. EtOH were added, stirred for 1 h; soln. was filtered and allowed to stand at room temp. for several days Zheng, Yue-Qing; Cheng, De-Yi; Liu, Bin-Bin; Huang, Wen-Xiang; Dalton Transactions; vol. 40; nb. 1; (2011); p.

277 - 286 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

25/96

2016-04-10 14:47:02

N

O 2

N

O–

O

N N

O

O–

N

2

H

N

N

N

N

H

Mn2+

N

N N

2H O 2

Mn2+

Rx-ID: 35578417 View in Reaxys 69/325 Yield

Conditions & References

74 %

in methanol, dichloromethane, Time= 0.5h Seth, Piya; Bauza, Antonio; Frontera, Antonio; Massera, Chiara; Gamez, Patrick; Ghosh, Ashutosh; CrystEngComm; vol. 15; nb. 15; (2013); p. 3031 - 3039 View in Reaxys

O

N N

4– O OH 2

N 2

N

6

O– 2

O

N

N

N

N

N

N

N

Mn2+ 3 Mn2+

N

Rx-ID: 35578418 View in Reaxys 70/325 Yield

Conditions & References

70 %

in methanol, dichloromethane, Time= 0.5h Seth, Piya; Bauza, Antonio; Frontera, Antonio; Massera, Chiara; Gamez, Patrick; Ghosh, Ashutosh; CrystEngComm; vol. 15; nb. 15; (2013); p. 3031 - 3039 View in Reaxys 2H

HO

HO O

O

2H

Rx-ID: 37003098 View in Reaxys 71/325 Yield

Conditions & References Stage 1: With AcOH-d4, palladium diacetate, sodium carbonate, Time= 12h, T= 120 °C , Sealed tube Stage 2: With sodium hydroxide in dichloromethane, water, Time= 12h, T= 120 °C , Sealed tube Ma, Sandy; Villa, Giorgio; Thuy-Boun, Peter S.; Homs, Anna; Yu, Jin-Quan; Angewandte Chemie - International Edition; vol. 53; nb. 3; (2014); p. 734 - 737; Angew. Chem.; vol. 126; nb. 3; (2013); p. 753 - 756,4 View in Reaxys

O

HO

K+

O–

O

Rx-ID: 39368386 View in Reaxys 72/325 Yield

Conditions & References With potassium hydroxide in water, Time= 0.5h, T= 20 °C Rouhi-Saadabad, Hamed; Akhlaghinia, Batool; Chemical Papers; vol. 69; nb. 3; (2015); p. 479 - 485 View in Reaxys

O F

HO NH 2

B F

F

HO O

Rx-ID: 438695 View in Reaxys 73/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

26/96

2016-04-10 14:47:02

Yield

Conditions & References With chloramine-T, T= 40 °C , Erhitzen des Reaktionsprodukts mit wss. Salzsaeure und Deuteriumoxid enthaltendem Wasser; Herstellung von (+-)-2.O-Dideuterio-2-phenyl-essigsaeure enthaltender Phenylessigsaeure Moss; Schoenheimer; Journal of Biological Chemistry; vol. 135; (1940); p. 415,417, 423 View in Reaxys

O

O

O

Na +

O–

H N

N

O O Cl

N

H

HO N O

O

N H

O

N

O O

Rx-ID: 2428687 View in Reaxys 74/325 Yield

Conditions & References in chloroform, water Echavarren, Antonio; Galan, Amalia; Lehn, Jean-Marie; Mendoza, Javier de; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4994 - 4995 View in Reaxys

HO O

13C

O

13C

O

Cl

Rx-ID: 2695282 View in Reaxys 75/325 Yield

Conditions & References With magnesium, Multistep reaction Chapman, Orville L.; Tsou, Uh-Po Eric; Journal of the American Chemical Society; vol. 106; nb. 25; (1984); p.

7974 - 7976 View in Reaxys

–

O

Ba2+

O

13C

HO

O–

Cl

13C

O

Rx-ID: 2696144 View in Reaxys 76/325 Yield

Conditions & References With magnesium, 1) ether, 2) ether, Yield given. Multistep reaction Chapman, Orville L.; Tsou, Uh-Po Eric; Johnson, Jeffery W.; Journal of the American Chemical Society; vol.

109; nb. 2; (1987); p. 553 - 559 View in Reaxys

13

N

C

HO

13C

O

Rx-ID: 4076681 View in Reaxys 77/325 Yield

Conditions & References With sodium hydroxide, Time= 18h, Heating, Yield given Holmes, Darren L.; Lightner, David A.; Tetrahedron; vol. 51; nb. 6; (1995); p. 1607 - 1622

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

27/96

2016-04-10 14:47:02

View in Reaxys With potassium hydroxide in ethanol, Heating, Yield given Kinoshita, Takeshi; Tetrahedron Letters; vol. 38; nb. 2; (1997); p. 259 - 262 View in Reaxys

–O

O

–O

O

O

Rx-ID: 4842300 View in Reaxys 78/325 Yield

Conditions & References With sodium hydroxide in ethanol, water, T= 42 °C , Rate constant Jackman, Lloyd M.; Chen, Xian; Journal of the American Chemical Society; vol. 119; nb. 37; (1997); p. 8681 8684 View in Reaxys 2H

2H

2H

N 2H

2H

HO O

2H

2H

2H 2H

2H

Rx-ID: 9020690 View in Reaxys 79/325 Yield

Conditions & References With potassium hydroxide in water, Heating Turro, Nicholas J.; Lei, Xue-Gong; Jockusch, Steffen; Li, Wei; Liu, Zhiqiang; Abrams, Lloyd; Ottaviani, M. Francesca; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2606 - 2618 View in Reaxys 2H

2H 2H

Cl 2H

2H 2H

2H

HO O

2H

2H 2H

Rx-ID: 14961705 View in Reaxys 80/325 Yield

Conditions & References Reaction Steps: 2 1: KOH / H2O / Heating With potassium hydroxide in water Turro, Nicholas J.; Lei, Xue-Gong; Jockusch, Steffen; Li, Wei; Liu, Zhiqiang; Abrams, Lloyd; Ottaviani, M. Francesca; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2606 - 2618 View in Reaxys

2H 2

N

n-hexyl halide

H

HO

O

Rx-ID: 16395597 View in Reaxys 81/325 Yield

Conditions & References Reaction Steps: 2 1: Bu4NBr, NaOD / H2O / 2 h / Ambient temperature 2: 74 percent / NaOD, Bu4NBr / D2O / 5 h / Heating With NaOD, tetrabutylammomium bromide in water, water-d2 Kim, Sung Soo; Tuchkin, Alexey; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3821 - 3824 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

28/96

2016-04-10 14:47:02

2H

HO

Br

Br

O 2H

Br

Rx-ID: 17335037 View in Reaxys 82/325 Yield

Conditions & References Reaction Steps: 3 1: 80 percent / H2O; ethanol 2: 90 percent / KOH / H2O / Heating 3: 1.) D2O, Na2CO3, 2.) 7.5percent NaOD, Zn / 1.) 80 deg C, 2 h, 2.) D2O, reflux, 36 h With potassium hydroxide, NaOD, water-d2, sodium carbonate, zinc in ethanol, water Moore, Bradley S.; Walker, Kevin; Tornus, Ingo; Handa, Sandeep; Poralla, Karl; Floss, Heinz G.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2173 - 2185 View in Reaxys

2H

HO

Br N

O 2H

Br

Rx-ID: 17349083 View in Reaxys 83/325 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / KOH / H2O / Heating 2: 1.) D2O, Na2CO3, 2.) 7.5percent NaOD, Zn / 1.) 80 deg C, 2 h, 2.) D2O, reflux, 36 h With potassium hydroxide, NaOD, water-d2, sodium carbonate, zinc in water Moore, Bradley S.; Walker, Kevin; Tornus, Ingo; Handa, Sandeep; Poralla, Karl; Floss, Heinz G.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2173 - 2185 View in Reaxys

HO 2H

O

2H

Rx-ID: 21517931 View in Reaxys 84/325 Yield

Conditions & References Reaction Steps: 3 1: NBS 2: aq. ethanol 3: hydrolysis With N-bromosuccinmide in ethanol Chao, Herbert S.-I.; Berchtold, Glenn A.; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1191 - 1194 View in Reaxys O–

2

O– O

O

N H

HN

Li+

O

O

O

OH O– O

O– 2 Li+

H 2N

N H

Rx-ID: 25972184 View in Reaxys 85/325 Yield

Conditions & References With hydrogenchloride, penicillin G acylase in methanol, water, Time= 20h, pH= 8 Soldermann, Carole Pissot; Vallinayagam, Ramakrishnan; Tzouros, Manuel; Neier, Reinhard; Journal of Organic Chemistry; vol. 73; nb. 2; (2008); p. 764 - 767

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

29/96

2016-04-10 14:47:02

View in Reaxys O–

N

N

4

3 Co 2+

HO

O 2

O

O

6H O Co 2+ 2 O–

5 N

N

HO

O

O 3.5

N

O

H

2 O

H

N

O–

O

Rx-ID: 27493272 View in Reaxys 86/325 Yield

Conditions & References

85 %

in water, High Pressure; aq. mixt. of 2-phenylmalonic acid, Co(NO3)2*6H2O, 4,4'-bipyridine placedin vessel, sealed, heated to 160°C for 3 d, cooled at 5°C /h to 100°C, held for 10 h, cooled to room temp.; ppt. filtered, dried in air; elem. anal.

Zheng, Yan-Zhen; Tong, Ming-Liang; Chen, Xiao-Ming; Journal of Molecular Structure; vol. 796; nb. 1-3; (2006); p. 9 - 17 ; (from Gmelin) View in Reaxys

O

HO

O– (v2) – O

O

O (v4)

(v3)

N 2+ (v5) Cu Cu 2+N N (v5) (v4) (v4)2- N C

(v4)

(v4)

O

Rx-ID: 31798529 View in Reaxys 87/325 Yield

Conditions & References Reaction Steps: 2 1: benzene 2: CO / dichloromethane With CO in dichloromethane, benzene Doyle, G.; Eriksen, K. A.; Modrick, M.; Ansell, G.; Organometallics; vol. 1; (1982); p. 1613 - 1618 View in Reaxys

O Ag+

H

O–

O

NH 2

HO

NH 2Cl

H

O H 2N

OH

O

NH 2

OH

Rx-ID: 33014874 View in Reaxys 88/325 Yield

Conditions & References 12 :L-ornithine monohydrochloride is dissolved in water at a concentration of 300 - 350 g/Kg (~3 volumes water). To the resulting solution is added 1 molar equivalent of silver phenyl acetate in 2.5 volumes DMSO (0.4 g/g) at room temperature within 2 hours. The receiver containing the solution is then washed with DMSO and added to the reaction mass. The silver chloride formed can be filtered through the reaction mass over a lens filter prepared with Celite and a GAF filter. After filtration, the filter is washed with an additional volume of water.[0177] In order to precipitate the final product, IPA is added to the reaction mass to a final concentration range of 65-95percent IPA. The reaction mass is then cooled to 0 + 3 °C within 6 hours, stirred for 1 hour and then the product isolated in a centrifuge.[0178] The isolated wet product is redisolved in an aqueous dilute HC1 solution (0.33percent) representing between 1-3.5 molar equivalents of HC1. The reaction mass is filtered over a lens filter prepared with Celite and a GAF filter to remove the silver chloride formed. After filtration, the filter is washed with an additional volume of water.[0179] To precipitate the final product, IPA is added again to the reaction mass to a final concentration range of 60-80percent IPA. The reaction mass is then cooled to 0 + 3 °C within 6 hours, stirred for 1 hour and then the product is isolated in a centrifuge. The final product is then dried at 40+5 °C for about 6.5 to 8 hours to provide crystalline L-ornithine phenyl acetate. in water, dimethyl sulfoxide, Time= 2h, T= 20 °C , Industry scale, Product distribution / selectivity

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

30/96

2016-04-10 14:47:02

Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith, H.; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2012/48043; (2012); (A1) English View in Reaxys

O– 3H O 2

O

O

P

3

P

Cl 3Ru

HO H–

Ru 2+

Rx-ID: 41003028 View in Reaxys 89/325 Yield

Conditions & References

51 %

With potassium hydroxide in ethanol, Time= 0.166667h, Reflux, Inert atmosphere, Schlenk technique Bai, Wei; Lee, Ka-Ho; Tse, Sunny Kai San; Chan, Ka Wing; Lin, Zhenyang; Jia, Guochen; Organometallics; vol.

34; nb. 15; (2015); p. 3686 - 3698 View in Reaxys Br

2

N

Mn2+ O– O

O–

O

OH

O–

N

Mn

O

N

Br

OH

–

N

Br

3+

Br

Rx-ID: 27248637 View in Reaxys 90/325 Yield

Conditions & References

82 %

in ethanol, reflux (2.5 h); filtration, concn., pptn. upon addn. to Et2O, washing (Et2O), drying (vac.); elem. anal.

Hulme, Charlotte E.; Watkinson, Michael; Haynes, Michaela; Pritchard, Robin G.; McAuliffe, Charles A.; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 11; (1997); p. 1805 1814 ; (from Gmelin) View in Reaxys OH

2

N

Mn2+ O– O

O–

O

N

O–

OH Mn

–

O

N

N

3+

Rx-ID: 27248638 View in Reaxys 91/325 Yield 81 %

Conditions & References in ethanol, reflux (2.5 h); filtration, concn., pptn. upon addn. to Et2O, washing (Et2O), drying (vac.); elem. anal.

Hulme, Charlotte E.; Watkinson, Michael; Haynes, Michaela; Pritchard, Robin G.; McAuliffe, Charles A.; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 11; (1997); p. 1805 1814 ; (from Gmelin) View in Reaxys

F

NH 2

H

HO

O– F

H O

O

H 2N

H O– –O

S OO

H

F

NH 2

H

2 O H 2N

Pt2+

H

F

Pt2+

Rx-ID: 27283682 View in Reaxys 92/325 Yield 55 %

Conditions & References in water, stoich. amts., stirring at room temp. for 1 d (pptn.); collection (filtration), recrystn. (66percent aq. MeOH, slow evapn. during 48 h), collection (filtration), drying (vac., over P2O5) Gust, Ronald; Krauser, Rudolf; Schmid, Beate; Schoenenberger, Helmut; Inorganica Chimica Acta; vol. 250; nb. 1-2 PART I; (1996); p. 203 - 218 ; (from Gmelin)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

31/96

2016-04-10 14:47:02

View in Reaxys

H 2N

F

H

H

H

HO

NH 2 O

O

H

F racemate O– –O

H 2N O–

S OO

Pt2+

F

H

H

2

NH 2

O F

racemate

Pt2+

Rx-ID: 27283687 View in Reaxys 93/325 Yield

Conditions & References

58 %

in water, stoich. amts., stirring at room temp. for 1 d (pptn.); collection (filtration), recrystn. (66percent aq. MeOH, slow evapn. during 48 h), collection (filtration), drying (vac., over P2O5) Gust, Ronald; Krauser, Rudolf; Schmid, Beate; Schoenenberger, Helmut; Inorganica Chimica Acta; vol. 250; nb. 1-2 PART I; (1996); p. 203 - 218 ; (from Gmelin) View in Reaxys O–

N 6 H

O

H2

O

N+

O

O

O–

OH O

4

4 N

HO

N

O–

HO

Zn 2+

O 2.5

N

O

H

2 O

H

N

O–

3 Zn 2+

O

Rx-ID: 27558039 View in Reaxys 94/325 Yield

Conditions & References

83 %

in water, High Pressure; aq. mixt. of 2-phenylmalonic acid, Zn(NO3)2*6H2O, 4,4'-bipyridine placedin vessel, sealed, heated to 160°C for 3 d, cooled at 5°C /h to 100°C, held for 10 h, cooled to room temp.; ppt. filtered, dried in air; elem. anal.

Zheng, Yan-Zhen; Tong, Ming-Liang; Chen, Xiao-Ming; Journal of Molecular Structure; vol. 796; nb. 1-3; (2006); p. 9 - 17 ; (from Gmelin) View in Reaxys

O

O

13C

Cl

HO

Mg

13C

O

Rx-ID: 4295149 View in Reaxys 95/325 Yield 70 %

Conditions & References in diethyl ether, Time= 2h Hoffmann, Reinhard W.; Dress, Ruprecht K.; Ruhland, Thomas; Wenzel, Andreas; Chemische Berichte; vol.

128; nb. 9; (1995); p. 861 - 870 View in Reaxys

HO

2H

O

O O

Rx-ID: 9060565 View in Reaxys 96/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

32/96

2016-04-10 14:47:02

Yield

Conditions & References in water-d2, T= 20 °C Flakus, Henryk T.; Chelmecki, Michal; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 58; nb. 9; (2002); p. 1867 - 1880 View in Reaxys 2

H

2H

2H

2H

HO

HO

O

Rx-ID: 11716301 View in Reaxys 97/325 Yield

Conditions & References Reaction Steps: 2 1: 91 percent / phosphorus tribromide With phosphorus tribromide Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 18; (1982); p. 317 - 324; Zhurnal Organicheskoi Khimii; vol. 18; nb. 2; (1982); p. 365 - 373 View in Reaxys Reaction Steps: 2 1: 59 percent / SOCl2, Pyridin / CHCl3 / 20 °C 2: 65 percent / Mg / diethyl ether / -30 °C With pyridine, thionyl chloride, magnesium in diethyl ether, chloroform Heesing, Albert; Muellers, Wolfgang; Chemische Berichte; vol. 113; nb. 1; (1980); p. 9 - 18 View in Reaxys

potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide>

Br

HO

13C

O

Rx-ID: 17594600 View in Reaxys 98/325 Yield

Conditions & References Reaction Steps: 2 2: KOH / ethanol / Heating With potassium hydroxide in ethanol Kinoshita, Takeshi; Tetrahedron Letters; vol. 38; nb. 2; (1997); p. 259 - 262 View in Reaxys

O 2

2 O–

N Cu 2+

O 3

2 N

2

H O

H

O–

Cu 2+

Rx-ID: 26324628 View in Reaxys 99/325 Yield

Conditions & References With pyridine in pyridine, solution in hot pyridine;; crystn. on cooling; dried on filter paper; Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys With pyridine in neat (no solvent), storage of Cu(C8H7O2)2*2C5H5N*2H2O and pyridine in a desiccator over solid NaOH; Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

33/96

2016-04-10 14:47:02

View in Reaxys

O

O CuI

N

N

O–

O– (v2) – O

Tl+

O (v4)

(v3)

N 2+ (v5) Cu Cu 2+N N (v5) (v4) (v4)2- N C

(v0)

(v4)

(v4)

O

Rx-ID: 27090477 View in Reaxys 100/325 Yield

Conditions & References With CO in dichloromethane, byproducts: TlI; suspn. of CuI was stirred for 30 min under CO; tmed was added, stirringfor 20 min; addn. of TlOCOCH2Ph; stirring under CO for 30 min; filtration, concn., pptn. with pentane; elem. anal.

Doyle, G.; Eriksen, K. A.; Modrick, M.; Ansell, G.; Organometallics; vol. 1; (1982); p. 1613 - 1618 ; (from Gmelin) View in Reaxys

HO

–O

O

O

2

2

Pb2+

O

Pb2+

O– (v0)

(v0)

Rx-ID: 28588187 View in Reaxys 101/325 Yield

Conditions & References

40 %

in methanol, Pb(II) acetate (1 mmol) and (C6H5)CH2COOH (1 mmol) in MeOH heated (60°C, 5-10 d) in branched tube; ppt. filtered off; washed with acetone; dried in air; elem. anal.

Haddadian, Hasan; Aslani, Alireza; Morsali, Ali; Inorganica Chimica Acta; vol. 362; nb. 6; (2009); p. 1805 - 1809 ; (from Gmelin) View in Reaxys

35 %

in methanol, Sonication; 0.3 M Pb(II) acetate (10 ml) sonicated (20 kHz, 600 W); 0.3 M (C6H5)CH2COOH (10 ml) added dropwise (1 h); ppt. filtered off; washed with MeOH; dried in air; elem. anal.; SEM Haddadian, Hasan; Aslani, Alireza; Morsali, Ali; Inorganica Chimica Acta; vol. 362; nb. 6; (2009); p. 1805 - 1809 ; (from Gmelin) View in Reaxys

HO

F O

B

F

HO O

F

Rx-ID: 66199 View in Reaxys 102/325 Yield

Conditions & References With diethyl ether, boron trifluoride Meerwein; Pannwitz; Journal fuer Praktische Chemie (Leipzig); vol. <2>141; (1934); p. 131,145 View in Reaxys With hydrogenchloride, water, water-d2, Herstellung von (+-)-2.O-Dideuterio-2-phenyl-essigsaeure enthaltender Phenylessigsaeure Moss; Schoenheimer; Journal of Biological Chemistry; vol. 135; (1940); p. 415,417, 423 View in Reaxys

O 3

2 N Cu 2+

O–

O 2

2 O–

N Cu 2+

2

H O

H

Rx-ID: 26323926 View in Reaxys 103/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

34/96

2016-04-10 14:47:02

Yield

Conditions & References With water in neat (no solvent) Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O 2

O 2

Cu 2+

O–

Cu 2+

O– H

H

2 O

H

N

H

H

Rx-ID: 26324467 View in Reaxys 104/325 Yield

Conditions & References With ammonia, water in ammonia, evaporation on air or over solid NaOH;; dried on filter paper and on air; Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O

O

2

2

Cu 2+

O–

2 O–

N Cu 2+

2

H O

H

Rx-ID: 26324468 View in Reaxys 105/325 Yield

Conditions & References With pyridine, water in pyridine, water, dissolving of Cu(C8H7O2)2 in aq. pyridine on slight warming;; cooling or evaporation over solid NaOH; dried on filter paper; Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

N

N

N N

10

O

N

N N

6 O

–

O 6

3 Cu 2+

N N

O–

3 Cu 2+

Rx-ID: 26647481 View in Reaxys 106/325 Yield

Conditions & References With pyridine in neat (no solvent), storage of 3Cu(C8H7O2)2*(CH2)6N4 and pyridine in a desiccator over P2O5 for 4 days; Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 7; (1933); p. 60 - 78 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

35/96

2016-04-10 14:47:02

H

3 HO

–

O

O

3

O

La

La 3+

3+

O

H

O

3 O–

Rx-ID: 26829285 View in Reaxys 107/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3 HO

O– 3

Pm3+

Pm3+

O

O

O

H

O

3 O–

Rx-ID: 26841712 View in Reaxys 108/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3 HO

–O

3

O

O

Nd 3+

Nd 3+

O

H

O

3 O–

Rx-ID: 26847848 View in Reaxys 109/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

36/96

2016-04-10 14:47:02

H

3 HO

–

O

O

3

Lu

O

Lu 3+

3+

O

H

O

3 O–

Rx-ID: 26847849 View in Reaxys 110/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3 HO

–O

O

3

Ho 3+

Ho 3+

O

O

H

O

3 O–

Rx-ID: 26847850 View in Reaxys 111/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3 HO

–O

3

O

O

Tb 3+

Tb 3+

O

H

O

3 O–

Rx-ID: 26847851 View in Reaxys 112/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

37/96

2016-04-10 14:47:02

H

3 HO

–

O

O

3

Yb3+

3+

Yb

O

O

H

O

3 O–

Rx-ID: 26847852 View in Reaxys 113/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3 HO

O

3 –O

O

Tm3+

Tm3+

O

H

O

3 O–

Rx-ID: 26847853 View in Reaxys 114/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3 HO

–O

3

O

O

Sm3+

Sm3+

O

H

O

3 O–

Rx-ID: 26847854 View in Reaxys 115/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

38/96

2016-04-10 14:47:02

H

3 HO

–

O

O

3

Pr

O

Pr3+

3+

O

H

O

3 O–

Rx-ID: 26847855 View in Reaxys 116/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

O

HO

–O

3

O

3

O

Gd 3+

O–

Gd 3+

3

H O

H

Rx-ID: 26847856 View in Reaxys 117/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

O

HO

–O

3

O

3

O

O–

Dy 3+

3

Dy 3+

H O

H

Rx-ID: 26847857 View in Reaxys 118/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

39/96

2016-04-10 14:47:02

O

HO

–

O

3

O

3

O

Eu3+

O–

Eu3+

H

3

O

H

Rx-ID: 26847858 View in Reaxys 119/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

O

HO

–O

3

O

3

O

O–

Er3+

Er3+

H

3

O

H

Rx-ID: 26847859 View in Reaxys 120/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3

O

H

HO O

3+

Y

O3Y2

O

3 O–

Rx-ID: 26847861 View in Reaxys 121/325 Yield

Conditions & References excess of phenylacetic acid, heated; filtered while hot, washed with water, air-dried Pratt, L. A.; James, C.; Journal of the American Chemical Society; vol. 33; (1911); p. 1330 - 1332 ; (from Gmelin) View in Reaxys excess of phenylacetic acid, heated; filtered while hot, washed with water, air-dried vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

40/96

2016-04-10 14:47:02

O

HO

–

O

3

O

3

O

Ce 3+

O–

Ce 3+

H

3

O

H

Rx-ID: 26847862 View in Reaxys 122/325 Yield

Conditions & References With ammonia in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp.

Pirkes, S. B.; Krasovskaya, T. A.; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 1465 - 1467; Zhurnal Neorganicheskoi Khimii; vol. 21; (1976); p. 2665 - 2669 ; (from Gmelin) View in Reaxys With NH3 in not given, water bath, pptn. from hot soln. with dild. NH3; filtered, washed with water, air-dried at room temp. vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

HO

O– O

2

Mn2+

O–

O–

O

Mn2+

O

Rx-ID: 27217902 View in Reaxys 123/325 Yield 57 %

Conditions & References in water, stirring (reflux, 6 h); filtration, washing (Et2O), evapn. of the aq. phase to dryness, grounding in a pestle and mortar, drying in vacuo over P2O5, drying in vacuo at 160°C for 4 h; elem. anal.

Hulme, Charlotte E.; Watkinson, Michael; Haynes, Michaela; Pritchard, Robin G.; McAuliffe, Charles A.; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 11; (1997); p. 1805 1814 ; (from Gmelin) View in Reaxys

HO

Cl

O

3

Nd Cl

(v3)

Cl

O– H

C H2

O

O

H

Nd 3+

Rx-ID: 27515671 View in Reaxys 124/325 Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys H

2 HO

O

Cl

O

Y Cl

(v3)

Cl

Y3+ 3

C H2

H

O– O

Rx-ID: 27516197 View in Reaxys 125/325 Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

41/96

2016-04-10 14:47:02

HO

Cl

O

3 Pr

Cl

(v3)

O– H

C H2

Cl

O

O

H

Pr3+

Rx-ID: 27516451 View in Reaxys 126/325 Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys

HO O

Ce Cl

O–

3

Cl (v3)

Ce 3+

C H2

Cl

O

H O

H

Rx-ID: 27517039 View in Reaxys 127/325 Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys

HO

Cl O

(v3)

Er

Cl

O–

3

Cl

Er3+

C H2 2

O

H O

H

Rx-ID: 27525904 View in Reaxys 128/325 Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys H

2 HO

O

Cl

O

Yb Cl Cl

Yb3+

(v3)

3

H

O–

C H2

O

Rx-ID: 27525992 View in Reaxys 129/325 Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys H

2

O

HO

Cl

O

Ho Cl

H

Cl

Ho 3+

(v3)

3

C H2

O– O

Rx-ID: 27526173 View in Reaxys 130/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

42/96

2016-04-10 14:47:02

Yield

Conditions & References With ammonium hydroxide in water, metal salt soln. addn. to org. acid soln. (pH 5 (aq.NH3)), stirring for 2 h at 65°C (water bath), filtration, filtrate keeping in air forseveral d; solid filtration off, washing (EtOH), drying over P2O5 in desiccator; elem. anal.

Wang; Niu; Liu; Ni; Thermochimica Acta; vol. 282-283; nb. SPEC. ISS.; (1996); p. 353 - 358 ; (from Gmelin) View in Reaxys

HO

2

–O

O

O

3 H

O

O

H 2

Pb2+

O–

Pb2+

(v0)

(v0)

Yield

Rx-ID: 28066048 View in Reaxys 131/325

Conditions & References

35 %

in methanol, react. lead salt with ligand in methanol at 60°C, crystn. for 5-10 d; filtration, washing with acetone, air drying; elem. anal.

Payehghadr, Mahmood; Yousefi, Sohaila; Morsali, Ali; Journal of Organometallic Chemistry; vol. 693; nb. 15; (2008); p. 2514 - 2518 ; (from Gmelin) View in Reaxys

N O

O HO N

H

O

O

H

2

HO

N

–O

O

2 H

O

H

O– N

2

N

Zn 2+

O

1.5H O 2

N

O N Zn 2+

N

Rx-ID: 38578675 View in Reaxys 132/325 Yield

Conditions & References

81 %

Time= 72h, T= 100 °C , Autoclave Guo, Wei; Han, Li-Qiang; Guo, Ya-Mei; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 539 - 547 View in Reaxys HO

O 2H

O

HO O

O

Rx-ID: 2092536 View in Reaxys 133/325 Yield

Conditions & References With water-d2, sodium hydride in dimethyl sulfoxide, paraffin, Ambient temperature Wladislaw, Blanka; Marzorati, Liliana; Donnici, Claudio L.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 24; (1993); p. 3167 - 3170 View in Reaxys

O O–

Li+

H C

O O–

Li+

Rx-ID: 3166176 View in Reaxys 134/325 Yield

Conditions & References With triphenylemethane, lithium carboxylate in tetrahydrofuran, N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 21h, Ambient temperature, free energy of the isodesmic process, Thermodynamic data, Equilibrium constant Renaud, Philippe; Fox, Marye Anne; Journal of the American Chemical Society; vol. 110; nb. 17; (1988); p. 5705 5709

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

43/96

2016-04-10 14:47:02

View in Reaxys 2H 2H

HO

(+-)-2-amino-3-<pentadeuterio-phenyl>-propionic acid

O

2

2

H

H

2H

Rx-ID: 8129609 View in Reaxys 135/325 Yield

Conditions & References With sodium-salt of toluene-sulfonic acid-(4)-chloroamide, in gepufferter wss. Loesung (pH 4.7) und Erhitzen des Reaktionsprodukts mit wss. Salzsaeure Moss; Schoenheimer; Journal of Biological Chemistry; vol. 135; (1940); p. 415,417, 423 View in Reaxys O

2

H

O

4'-dimethylamino-biphenyl-4-yl magnesium iodide

2H

HO

O

Rx-ID: 11714383 View in Reaxys 136/325 Yield

Conditions & References Reaction Steps: 3 1: 85 percent / lithium aluminum deuteride / diethyl ether 2: 91 percent / phosphorus tribromide With lithium aluminium deuteride, phosphorus tribromide in diethyl ether Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 18; (1982); p. 317 - 324; Zhurnal Organicheskoi Khimii; vol. 18; nb. 2; (1982); p. 365 - 373 View in Reaxys H

13C 2

HO 13C

O

O

Rx-ID: 13904661 View in Reaxys 137/325 Yield

Conditions & References Reaction Steps: 3 1: 88 percent / t-BuOK / benzene / 16 h / 20 °C 2: 79 percent / CH3SO2N3; Et3N / H2O; acetonitrile / 2.5 h / 20 °C 3: dioxane; H2O / 0.75 h / Irradiation With potassium tert-butylate, triethylamine, Methanesulfonyl azide in 1,4-dioxane, water, acetonitrile, benzene Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

HO 13

C

O

13C

O

Rx-ID: 13904662 View in Reaxys 138/325 Yield

Conditions & References Reaction Steps: 3 1: 88 percent / t-BuOK / benzene / 16 h / 20 °C 2: 79 percent / CH3SO2N3; Et3N / H2O; acetonitrile / 2.5 h / 20 °C 3: dioxane; H2O / 0.75 h / Irradiation With potassium tert-butylate, triethylamine, Methanesulfonyl azide in 1,4-dioxane, water, acetonitrile, benzene Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

44/96

2016-04-10 14:47:02

View in Reaxys H

13C 2

HO

O 13C

O

HO

Rx-ID: 13905382 View in Reaxys 139/325 Yield

Conditions & References Reaction Steps: 4 1: 81 percent / diethyl ether / 2 h / 20 °C 2: 88 percent / t-BuOK / benzene / 16 h / 20 °C 3: 79 percent / CH3SO2N3; Et3N / H2O; acetonitrile / 2.5 h / 20 °C 4: dioxane; H2O / 0.75 h / Irradiation With potassium tert-butylate, triethylamine, Methanesulfonyl azide in 1,4-dioxane, diethyl ether, water, acetonitrile, benzene Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

HO

O 13C

13C

O

HO

Rx-ID: 13905383 View in Reaxys 140/325 Yield

Conditions & References Reaction Steps: 4 1: 81 percent / diethyl ether / 2 h / 20 °C 2: 88 percent / t-BuOK / benzene / 16 h / 20 °C 3: 79 percent / CH3SO2N3; Et3N / H2O; acetonitrile / 2.5 h / 20 °C 4: dioxane; H2O / 0.75 h / Irradiation With potassium tert-butylate, triethylamine, Methanesulfonyl azide in 1,4-dioxane, diethyl ether, water, acetonitrile, benzene Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

F

O

O 13C

F

H

13C 2

HO

F

O

Rx-ID: 13925815 View in Reaxys 141/325 Yield

Conditions & References Reaction Steps: 2 1: 79 percent / CH3SO2N3; Et3N / H2O; acetonitrile / 2.5 h / 20 °C 2: dioxane; H2O / 0.75 h / Irradiation With triethylamine, Methanesulfonyl azide in 1,4-dioxane, water, acetonitrile Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

F

O

O 13C

F F

HO

13C

O

Rx-ID: 13925816 View in Reaxys 142/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

45/96

2016-04-10 14:47:02

Yield

Conditions & References Reaction Steps: 2 1: 79 percent / CH3SO2N3; Et3N / H2O; acetonitrile / 2.5 h / 20 °C 2: dioxane; H2O / 0.75 h / Irradiation With triethylamine, Methanesulfonyl azide in 1,4-dioxane, water, acetonitrile Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys 2

H

O

2.3-epoxy-2.3-diphenyl-propionimidic acid methyl ester O

2H

HO

O

Rx-ID: 19960025 View in Reaxys 143/325 Yield

Conditions & References Reaction Steps: 3 1: 90 percent / LiAlD4 / diethyl ether / Heating 2: 59 percent / SOCl2, Pyridin / CHCl3 / 20 °C 3: 65 percent / Mg / diethyl ether / -30 °C With pyridine, thionyl chloride, lithium aluminium deuteride, magnesium in diethyl ether, chloroform Heesing, Albert; Muellers, Wolfgang; Chemische Berichte; vol. 113; nb. 1; (1980); p. 9 - 18 View in Reaxys 2H

2H

O HO O 2H

HO

O

O

Rx-ID: 20750743 View in Reaxys 144/325 Yield

Conditions & References Reaction Steps: 2 1: D2O / dioxane / 24 h / 30 °C 2: 85 percent / 180 °C With water-d2 in 1,4-dioxane McCarthy, Daniel G.; Hegarty, Anthony F.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 579 - 591 View in Reaxys

O

O

–O

O

O–

O

O

O–

–O

O

Rx-ID: 26187422 View in Reaxys 145/325 Yield 0%

Conditions & References With {Et4N}2{Fe4S4(SCH2Ph)4} in N,N-dimethyl-formamide, byproducts: S(2-); Electrolysis; electrolysis of a soln. of the cluster compd. during bubbling CO2 through the soln.; addn. of water, filtn., HPLC anal. of the filtrate Nakazawa, Makoto; Mizobe, Yasushi; Matsumoto, Yoichi; Uchida, Yasuzo; Tezuka, Meguru; Hidai, Masanobu; Bulletin of the Chemical Society of Japan; vol. 59; nb. 3; (1986); p. 809 - 814 ; (from Gmelin) View in Reaxys

Cu 2+

HO O

2

N N

O

O

(v1)

O

N

-1 O

N N

6 O–

3 Cu 2+

Rx-ID: 26591102 View in Reaxys 146/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

46/96

2016-04-10 14:47:02

Yield

Conditions & References With 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane in nitric acid, addn. of (CH2)6N4 to an aq. soln. of Cu(NO3)2; addn. of dild. HNO3; the acidic soln. is poured in a boiling soln. phenylacetic acid in alc./H2O; boiling;; sepn. of crystals after 24 h; washed with hot alcohol containing H2O; dried on air; Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 6; (1931); p. 286 - 298 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

3

H2 C Ti

O

(v2)

3

C H2

O

O–

2

C H2

O

Ti2+

Rx-ID: 27086728 View in Reaxys 147/325 Yield

Conditions & References With carbon dioxide in toluene, argon atmosphere or vac.; CO2 passing through Ti-complex soln. at 20°C for 20 h, pptn. on hexane addn. to reaction mixt.; ppt. filtration off, drying; elem. anal.

Razuvaev, G. A.; Vyshinskaya, L. I.; Vasil'eva, G. A.; Malysheva, A. V.; Rabinovich, A. M.; Journal of General Chemistry USSR (English Translation); vol. 52; (1982); p. 1178 - 1184; Zhurnal Obshchei Khimii; vol. 52; (1982); p.

1338 - 1345 ; (from Gmelin) View in Reaxys

3

3

H2 C Zr C (v2) H 2

O

O

O–

2

C H2

O

Zr 2+

Rx-ID: 27660873 View in Reaxys 148/325 Yield

Conditions & References With carbon dioxide in toluene, argon atmosphere or vac.; dry CO2 passing through Zr-complex soln. at 20°C for 20 h Razuvaev, G. A.; Vyshinskaya, L. I.; Vasil'eva, G. A.; Malysheva, A. V.; Rabinovich, A. M.; Journal of General Chemistry USSR (English Translation); vol. 52; (1982); p. 1178 - 1184; Zhurnal Obshchei Khimii; vol. 52; (1982); p.

1338 - 1345 ; (from Gmelin) View in Reaxys

O HO

O O

HN N H

O

O

OH

N

O

N

HN

Se

Se N

N

N H

N

N

Rx-ID: 28897131 View in Reaxys 149/325 Yield

Conditions & References in chloroform Goswami, Shyamaprosad; Hazra, Anita; Chakrabarty, Rinku; Fun, Hoong-Kun; Organic Letters; vol. 11; nb. 19; (2009); p. 4350 - 4353 View in Reaxys O

O–

O

O

N

HN

Se

O O

N

HN N H

O Se

N

N

N H

N

N

O– N+ N+

Rx-ID: 28897136 View in Reaxys 150/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

47/96

2016-04-10 14:47:02

Yield

Conditions & References in chloroform Goswami, Shyamaprosad; Hazra, Anita; Chakrabarty, Rinku; Fun, Hoong-Kun; Organic Letters; vol. 11; nb. 19; (2009); p. 4350 - 4353 View in Reaxys

O O– NH 2

O

HN

N+

N H

Rx-ID: 32493489 View in Reaxys 151/325 Yield

Conditions & References Reaction Steps: 6 1: 4-(N,N-dimethlyamino)pyridine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane 2: trifluoroacetic acid / dichloromethane / 2 h 3: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 2 h 4: Amberlite Ira-400 chloride 5: sodium hydroxide / methanol; water 6: methanol; water / 1 h With 4-(N,N-dimethlyamino)pyridine, 18-crown-6 ether, potassium carbonate, benzotriazol-1-ol, dicyclohexyl-carbodiimide, trifluoroacetic acid, sodium hydroxide in methanol, dichloromethane, water, N,N-dimethyl-formamide Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

O H N

O

OH O O–

H

O

O

HN

N+

N H

HN

Rx-ID: 32493496 View in Reaxys 152/325 Yield

Conditions & References Reaction Steps: 6 1: 4-(N,N-dimethlyamino)pyridine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane 2: trifluoroacetic acid / dichloromethane / 2 h 3: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 2 h 4: Amberlite Ira-400 chloride 5: sodium hydroxide / methanol; water 6: methanol; water / 1 h With 4-(N,N-dimethlyamino)pyridine, 18-crown-6 ether, potassium carbonate, benzotriazol-1-ol, dicyclohexyl-carbodiimide, trifluoroacetic acid, sodium hydroxide in methanol, dichloromethane, water, N,N-dimethyl-formamide Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

48/96

2016-04-10 14:47:02

NH H NH 2 NH

O

O O– O

HN

N H

N+

Rx-ID: 32493503 View in Reaxys 153/325 Yield

Conditions & References Reaction Steps: 4 1: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 2 h 2: Amberlite Ira-400 chloride 3: sodium hydroxide / methanol; water 4: methanol; water / 1 h With 18-crown-6 ether, potassium carbonate, sodium hydroxide in methanol, water, N,N-dimethyl-formamide Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

NH O H

O NH

O

NH

O O– O

HN

N+

N H

Rx-ID: 32493510 View in Reaxys 154/325 Yield

Conditions & References Reaction Steps: 5 1: trifluoroacetic acid / dichloromethane / 2 h 2: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 2 h 3: Amberlite Ira-400 chloride 4: sodium hydroxide / methanol; water 5: methanol; water / 1 h With 18-crown-6 ether, potassium carbonate, trifluoroacetic acid, sodium hydroxide in methanol, dichloromethane, water, N,N-dimethyl-formamide Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

49/96

2016-04-10 14:47:02

NH Cl – H

HN

N+

O

O O– O

N H

N+

HN

Rx-ID: 32493517 View in Reaxys 155/325 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide / methanol; water 2: methanol; water / 1 h With sodium hydroxide in methanol, water Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

NH I– H

HN

N+

O

O O– O

N+

HN

N H

Rx-ID: 32493523 View in Reaxys 156/325 Yield

Conditions & References Reaction Steps: 3 1: Amberlite Ira-400 chloride 2: sodium hydroxide / methanol; water 3: methanol; water / 1 h With sodium hydroxide in methanol, water Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

O

HO O

HORb

O–

Rb +

Rx-ID: 35628656 View in Reaxys 157/325 Yield

Conditions & References in water, T= 70 °C Regulska; Swislocka; Samsonowicz; Lewandowski; Journal of Molecular Structure; vol. 1044; (2013); p. 173 180

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

50/96

2016-04-10 14:47:02

View in Reaxys O– O

HO O

Cs +

CsHO

Rx-ID: 35628657 View in Reaxys 158/325 Yield

Conditions & References in water, T= 70 °C Regulska; Swislocka; Samsonowicz; Lewandowski; Journal of Molecular Structure; vol. 1044; (2013); p. 173 180 View in Reaxys

O

HO O

HLiO

O–

Li+

Rx-ID: 35628658 View in Reaxys 159/325 Yield

Conditions & References in water, T= 70 °C Regulska; Swislocka; Samsonowicz; Lewandowski; Journal of Molecular Structure; vol. 1044; (2013); p. 173 180 View in Reaxys

O

HO O

HNaO

O–

Na +

Rx-ID: 35628659 View in Reaxys 160/325 Yield

Conditions & References in water, T= 70 °C Regulska; Swislocka; Samsonowicz; Lewandowski; Journal of Molecular Structure; vol. 1044; (2013); p. 173 180 View in Reaxys

O

HO O

HKO

O–

K+

Rx-ID: 35628660 View in Reaxys 161/325 Yield

Conditions & References in water, T= 70 °C Regulska; Swislocka; Samsonowicz; Lewandowski; Journal of Molecular Structure; vol. 1044; (2013); p. 173 180 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

51/96

2016-04-10 14:47:02

O– O N+

O

OH

E

S

HO O

E

HO

Rx-ID: 35714259 View in Reaxys 162/325 Yield

Conditions & References Reaction Steps: 2 1: 1,1'-carbonyldiimidazole 2: dichloromethane-d2 / -98.16 °C With 1,1'-carbonyldiimidazole in dichloromethane-d2 Koeppe, Benjamin; Guo, Jing; Tolstoy, Peter M.; Denisov, Gleb S.; Limbach, Hans-Heinrich; Journal of the American Chemical Society; vol. 135; nb. 20; (2013); p. 7553 - 7566 View in Reaxys

O

HO

2 O–

O

Zn 2+

Rx-ID: 36525427 View in Reaxys 163/325 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide / water / pH 8.0 2: water / pH 3.0 With sodium hydroxide in water Cui, Xiaoneng; Zhao, Jianzhang; Yang, Pei; Sun, Jifu; Chemical Communications; vol. 49; nb. 87; (2013); p.

10221 - 10223 View in Reaxys

N O

O 2

HO N

H

O

O

O Cd 2+

H

HO

N

–O

2 H

O

O

O– N

2

N

H

Cd 2+

N

O N

H 2O

N

Rx-ID: 38578674 View in Reaxys 164/325 Yield 70 %

Conditions & References Time= 72h, T= 100 °C , Autoclave Guo, Wei; Han, Li-Qiang; Guo, Ya-Mei; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 539 - 547 View in Reaxys

HO

HO O

H 2N

H 2N

O

Rx-ID: 770952 View in Reaxys 165/325 Yield

Conditions & References Gibbs; Journal of the American Chemical Society; vol. 28; (1906); p. 1411 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

52/96

2016-04-10 14:47:02

2H

Cl HO

HO O

O

Cl

2H

Rx-ID: 4674486 View in Reaxys 166/325 Yield

Conditions & References With NaOD, nickel monoaluminide, water-d2, sodium carbonate, 1.) 80 deg C, 3 h, 2.) D2O, 80 deg C, 36 h, 3.) D2O, room temperature, 30 min, Yield given. Multistep reaction Moore, Bradley S.; Walker, Kevin; Tornus, Ingo; Handa, Sandeep; Poralla, Karl; Floss, Heinz G.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2173 - 2185 View in Reaxys

HO

Br

2

HO

O

H

O 2H

Br

Rx-ID: 4696464 View in Reaxys 167/325 Yield

Conditions & References With NaOD, water-d2, sodium carbonate, zinc, 1.) 80 deg C, 2 h, 2.) D2O, reflux, 36 h, Yield given. Multistep reaction Moore, Bradley S.; Walker, Kevin; Tornus, Ingo; Handa, Sandeep; Poralla, Karl; Floss, Heinz G.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2173 - 2185 View in Reaxys

HO 2H

O

Br

2H

Rx-ID: 21543730 View in Reaxys 168/325 Yield

Conditions & References Reaction Steps: 2 1: aq. ethanol 2: hydrolysis in ethanol Chao, Herbert S.-I.; Berchtold, Glenn A.; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1191 - 1194 View in Reaxys

2

Al2Ca 3O6

H

-1

O Ca 2+

O–

O–

0.5

CaO

C H2

O

H

O

Al2Ca 3.5HO 7

Rx-ID: 26370205 View in Reaxys 169/325 Yield

Conditions & References With H2O in water Poellmann, H.; Zeitschrift fuer Kristallographie; vol. 186; (1989); p. 236 - 237 ; (from Gmelin) View in Reaxys

O OH 2

O

P

P

2

–

O

O– O Cu +

Cu +

Rx-ID: 26952926 View in Reaxys 170/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

53/96

2016-04-10 14:47:02

Yield

Conditions & References in tetrahydrofuran, Kinetics, byproducts: CO2; inert atmosphere, 55.4 °C Darensbourg, Donald J.; Holtcamp, Matthew W.; Khandelwal, Bandana; Klausmeyer, Kevin K.; Reibenspies, Joseph H.; Inorganic Chemistry; vol. 34; (1995); p. 2389 - 2398 ; (from Gmelin) View in Reaxys

HO O

O

O

P 2

P 2

–O

–O

Cu +

Cu +

Rx-ID: 27162798 View in Reaxys 171/325 Yield

Conditions & References in tetrahydrofuran, Kinetics, byproducts: CO2; inert atmosphere, 55.4 °C Darensbourg, Donald J.; Holtcamp, Matthew W.; Khandelwal, Bandana; Klausmeyer, Kevin K.; Reibenspies, Joseph H.; Inorganic Chemistry; vol. 34; (1995); p. 2389 - 2398 ; (from Gmelin) View in Reaxys O–

6 H HO HO

H

O– N+

O

O

OH

11

HH

HH

O

(v7) O Mn

16 O–

O

Mn16O16( 22+)

Rx-ID: 27407114 View in Reaxys 172/325 Yield

Conditions & References

7.5 %

in methanol, byproducts: H2O; Mn compd. was added to stirred soln. of acid in MeOH; stirred for 5 min;left undisturbed at ambient temp. for 2 d King, Philippa; Wernsdorfer, Wolfgang; Abboud, Khalil A.; Christou, George; Inorganic Chemistry; vol. 43; nb.

23; (2004); p. 7315 - 7323 ; (from Gmelin) View in Reaxys O–

6 H

OH

11

HH

H

O–

6

HH

H

OH

6

HH

H

O 4

16 O–

HH

H O

O

H

16 O– Mn16O16( 22+)

Mn16O16( 22+)

Rx-ID: 27458389 View in Reaxys 173/325 Yield

Conditions & References in methanol, filtered; washed (EtOH); dried (vac.); elem. anal.

King, Philippa; Wernsdorfer, Wolfgang; Abboud, Khalil A.; Christou, George; Inorganic Chemistry; vol. 43; nb.

23; (2004); p. 7315 - 7323 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

54/96

2016-04-10 14:47:02

O– O N+ –O

O

OH

E

N+

O

S

S E

O

HO

Rx-ID: 35714254 View in Reaxys 174/325 Yield

Conditions & References in dichloromethane-d2, T= -98.16 °C , Solvent Koeppe, Benjamin; Guo, Jing; Tolstoy, Peter M.; Denisov, Gleb S.; Limbach, Hans-Heinrich; Journal of the American Chemical Society; vol. 135; nb. 20; (2013); p. 7553 - 7566 View in Reaxys O

N

O O–

HO

O

O 13C

N

O

13C

OH

OH

O

N+

Rx-ID: 35714266 View in Reaxys 175/325 Yield

Conditions & References in dichloromethane-d2, T= -98.16 °C , Solvent Koeppe, Benjamin; Guo, Jing; Tolstoy, Peter M.; Denisov, Gleb S.; Limbach, Hans-Heinrich; Journal of the American Chemical Society; vol. 135; nb. 20; (2013); p. 7553 - 7566 View in Reaxys O

O

N

O–

13C

O

N

OH

Cl

O

–O

13C

OH

N+

O

Cl

O N+

Rx-ID: 35714298 View in Reaxys 176/325 Yield

Conditions & References in dichloromethane-d2, T= -98.16 °C , Solvent Koeppe, Benjamin; Guo, Jing; Tolstoy, Peter M.; Denisov, Gleb S.; Limbach, Hans-Heinrich; Journal of the American Chemical Society; vol. 135; nb. 20; (2013); p. 7553 - 7566 View in Reaxys

NH 2

HO

H 2N

H

O

O

OH

Rx-ID: 37868747 View in Reaxys 177/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

55/96

2016-04-10 14:47:02

Yield

Conditions & References in methanol, T= 20 °C , Sonication Adalder, Tapas Kumar; Dastidar, Parthasarathi; Crystal Growth and Design; vol. 14; nb. 5; (2014); p. 2254 - 2262 View in Reaxys

NH 2

HO

O H

O

OH

H 2N

Rx-ID: 37868754 View in Reaxys 178/325 Yield

Conditions & References in methanol, T= 20 °C , Sonication Adalder, Tapas Kumar; Dastidar, Parthasarathi; Crystal Growth and Design; vol. 14; nb. 5; (2014); p. 2254 - 2262 View in Reaxys O –HC

HO

O– Mg2+

Mg Cl

O

Rx-ID: 1623603 View in Reaxys 179/325 Yield

Conditions & References in tetrahydrofuran, Time= 1h, Ambient temperature Toullec, Jean; Mladenova, Margarita; Gaudemar-Bardone, Francoise; Blagoev, Blagoi; Journal of Organic Chemistry; vol. 50; nb. 14; (1985); p. 2563 - 2569 View in Reaxys

HO

O– Tl+

O Tl+

O–

O (v0)

(v0)

Rx-ID: 26905495 View in Reaxys 180/325 Yield

Conditions & References in benzene Doyle, G.; Eriksen, K. A.; Modrick, M.; Ansell, G.; Organometallics; vol. 1; (1982); p. 1613 - 1618 ; (from Gmelin) View in Reaxys

Cl

2 Cl

HH

(v3) N N (v4) O (v4) H B–N N Fe 2+ (v5) (v4) N N – O O (v2)

O

O

N

N

H B–N N

N N

O

O–

O– Fe 3+

Rx-ID: 27459591 View in Reaxys 181/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

56/96

2016-04-10 14:47:02

Yield

Conditions & References in not given, byproducts: CO2; at ambient temp. for 1 h; not isolated, detected by UV-vis, ESR, MS Paine, Tapan K.; Zheng, Hui; Que Jr., Lawrence; Inorganic Chemistry; vol. 44; nb. 3; (2005); p. 474 - 476 ; (from Gmelin) View in Reaxys

HO

O

O–

2

Mn2+

O

O–

O

H O

O–

H

Mn2+

Rx-ID: 33139756 View in Reaxys 182/325 Yield

Conditions & References in water, MnCO3 was added to aq. soln. PhCH2COOH; soln. was filtered, heated on water bath and cooled to room temp., ppt. was filtered and dried in vacuo Kar, Paramita; Haldar, Ritesh; Gomez-Garcia, Carlos J.; Ghosh, Ashutosh; Inorganic Chemistry; vol. 51; nb. 7; (2012); p. 4265 - 4273 ; (from Gmelin) View in Reaxys

O

O

11C

Cl

HO

Mg

11C

O

Rx-ID: 3841437 View in Reaxys 183/325 Yield

Conditions & References With water, 1.) THF, 0 deg C, Yield given. Multistep reaction Halldin, C.; Langstroem, B.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 1; (1984); p. 1 - 4 View in Reaxys in diethyl ether, Carboxylation Jonson; Jones; Welch; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. SUPPL. 1; (1999); p. S710-S712 View in Reaxys

HO HO O

H OH

HO

H O

O

H O

OH

HO

H OH

O

OH

O

OH

H

HO

O

O H

HO OH

O

HO

OH

OHHO

H O HO

H

O

H

O

OH

O

HO

H H

H O

O OH HO

OH

O O

O O

OH

OH

OH

O

HO

HO

O

HO

OH

HO

O

O

HO

OH

HO

OH

O

O

O

HO

OH

O

HO O

HO

H

HO

OH

H

OH

O

O

OH

OH HO

Rx-ID: 4754635 View in Reaxys 184/325 Yield

Conditions & References With phosphate buffer in water-d2, T= 25 °C , standard molar enthalpy ΔrH0, standard molar Gibbs energy ΔrG0, standard molar entropy ΔrS0, Equilibrium constant, Thermodynamic data Rekharsky, Mikhail V.; Mayhew, Martin P.; Goldberg, Robert N.; Ross, Philip D.; Yamashoji, Yuko; Inoue, Yoshihisa; Journal of Physical Chemistry B; vol. 101; nb. 1; (1997); p. 87 - 100 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

57/96

2016-04-10 14:47:02

2 O–

O

2 Ni 2+

H

NH 2

H

NH 2

H N 2 2 H

H NH 2

O–

O

Ni 2+

Rx-ID: 26702361 View in Reaxys 185/325 Yield

Conditions & References in ethanol, water, prepn. from concd. meso-stilbenediamine-soln. in alc. and Ni-phenylacetate in H2O at 5 °C;; pptn., storing for 2 h, recrystn. from CHCl4; Hein, F.; Mueller, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 283; (1956); p. 172 - 187 ; (from Gmelin) View in Reaxys in ethanol, water, prepn. from concd. meso-stilbenediamine-soln. in alc. and Ni-phenylacetate in H2O at 5 °C;; pptn., storing for 2 h, recrystn. from CHCl4; vol. Ni: MVol.C1; 87, page 206 - 208 ; (from Gmelin) View in Reaxys

O

NH 2 2 O–

2

2

O–

Ni 2+

H

NH 2

O

NH 2 H NH 2

Ni 2+

Rx-ID: 26733772 View in Reaxys 186/325 Yield

Conditions & References in ethanol, water, prepn. from ice-cooled soln. of Ni-phenylacetate in H2O and α,α'-dimethylstilbene in alc.;; pptn.

Hein, F.; Mueller, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 283; (1956); p. 172 - 187 ; (from Gmelin) View in Reaxys in ethanol, water, prepn. from ice-cooled soln. of Ni-phenylacetate in H2O and α,α'-dimethylstilbene in alc.;; pptn. vol. Ni: MVol.C1; 87, page 206 - 208 ; (from Gmelin) View in Reaxys O– O

HO

Br

O

Fe

Br–

Fe 2+

Rx-ID: 26878386 View in Reaxys 187/325 Yield

Conditions & References byproducts: H2, C6H5CH2COOC2H5; Fe was treated with a mixt. of acid and EtBr at 200°C under unhydrous conditions; elem. anal.

Yamamoto, Takakazu; Imaizumi, Kimio; Kurata, Yasundo; Inorganica Chimica Acta; vol. 77; (1983); p. L3 - L4 ; (from Gmelin) View in Reaxys in neat (no solvent, solid phase), byproducts: C6H5CH2COOEt, H2; an iron plate was exposed to vapor contg. aromatic acid and EtBr at 200°C; crystals produced on the surface of the iron plate; elem. anal.

Yamamoto, Takakazu; Imaizumi, Kimio; Kurata, Yasundo; Inorganica Chimica Acta; vol. 85; (1984); p. 175 180 ; (from Gmelin)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

58/96

2016-04-10 14:47:02

View in Reaxys O

O

Cl –

S

HO O –O

–O

Na +

O–

Zr 4+

O

H

O–

O

O–

H

0.2

S

Zr 4+

P– OO

H 0.2O0.2( 0.2-)

P – OO

0.8 O O–

Rx-ID: 27430494 View in Reaxys 188/325 Yield

Conditions & References in water, dimethyl sulfoxide, 75°C, 3 days; ppt. was centrifuged, washed with DMSO-water (1:1), and dried at 80°C; elem. anal.

Vivani, Riccardo; Masci, Silvia; Alberti, Giulio; Inorganic Chemistry; vol. 43; nb. 1; (2004); p. 368 - 374 ; (from Gmelin) View in Reaxys O–

N 6

O

H O

O 2

2

HO

H

OH O N

N

HO

Cl 2Co

O Co 2+ 2

N

H O

H

Rx-ID: 27558040 View in Reaxys 189/325 Yield

Conditions & References

15 %

in water, High Pressure; aq. mixt. of 2-phenylmalonic acid, CoCl2*6H2O, 4,4'-bipyridine placed invessel, sealed, heated to 160°C for 3 d, cooled at 5°C/h to 100°C, held for 10 h, cooled to room temp.; filtered, mother liquid stood for 1 wk, ppt. filtered, dried in air; elem. anal.

Zheng, Yan-Zhen; Tong, Ming-Liang; Chen, Xiao-Ming; Journal of Molecular Structure; vol. 796; nb. 1-3; (2006); p. 9 - 17 ; (from Gmelin) View in Reaxys N

6H O Co 2+ 2 O NH N

2

N

O–

O

H N

O 4

HO

H

O

HO

2

H

O– 2 Co 2+

O

O

N

N H O

H

Rx-ID: 28069109 View in Reaxys 190/325 Yield 34 %

Conditions & References in water, High Pressure; under hydrothermal conditions; Co salt, NH(C5H4N)2 and PhCH(CO2H)2 addedto distd.

H2O in Parr acid digestion bomb; sealed; heated at 120.degree .C for 72 h; gradually cooled to ambient temp.; filtered; ppt. washed with distd. H2O and acetone; dried in air; elem. anal.

Johnston, Lindsey L.; Brown, Kyalamboka A.; Martin, David P.; LaDuca, Robert L.; Journal of Molecular Structure; vol. 882; nb. 1-3; (2008); p. 80 - 87 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

59/96

2016-04-10 14:47:02

N O

O HO N

H

O

O

2

H

HO

N

–O

O

4 H

O

H

O– N

2

N

Mn2+

O

2H O 2

N

O N Mn2+

N

Rx-ID: 38578669 View in Reaxys 191/325 Yield

Conditions & References

43 %

Time= 72h, T= 100 °C , Autoclave Guo, Wei; Han, Li-Qiang; Guo, Ya-Mei; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 539 - 547 View in Reaxys 2H

2H

2H

O NH 2 2H

2

HO

H

O

2H

2H

2H 2H

2H

Rx-ID: 3609953 View in Reaxys 192/325 Yield

Conditions & References With water Lere-Porte, J. P.; Bonniol, A.; Petrissans, J.; Journal of Molecular Structure; vol. 98; (1983); p. 77 - 88 View in Reaxys

O

HO (v2)

2

Zn

O

Zn 2+

O–

Rx-ID: 26159289 View in Reaxys 193/325 Yield

Conditions & References in tetrahydrofuran, N2 Wang, Dongren; Wurst, Klaus; Buchmeiser, Michael R.; Journal of Organometallic Chemistry; vol. 689; nb. 12; (2004); p. 2123 - 2130 ; (from Gmelin) View in Reaxys

O 3

O

2

2

O–

N

O–

N Cu 2+

Cu 2+

Rx-ID: 26323925 View in Reaxys 194/325 Yield

Conditions & References in neat (no solvent), on air; Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O 2

O

2 N Cu 2+

2

O– N

2

H O

H

O–

Cu 2+

Rx-ID: 26324627 View in Reaxys 195/325 Yield

Conditions & References in neat (no solvent), on air;

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

60/96

2016-04-10 14:47:02

Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O

N N

N N

O

N

6

N

O–

N N

6 O–

H 3 Cu 2+

10

H N

3 Cu 2+

H

7

H

N

H

H

Rx-ID: 26644294 View in Reaxys 196/325 Yield

Conditions & References in neat (no solvent), standing on air for 6 weeks; Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 7; (1933); p. 60 - 78 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O

N N

N N

O

N

6

N

O–

N N

6 O–

H 3 Cu 2+

12

H N

3 Cu 2+

H

7

H

N

H

H

Rx-ID: 26647084 View in Reaxys 197/325 Yield

Conditions & References in neat (no solvent), standing on air for a longer period of time; Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 7; (1933); p. 60 - 78 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

N 10

N N

N 2

N N

N N

O 6 O–

N N

O 6

3 Cu 2+

3 Cu 2+

O–

Rx-ID: 26647434 View in Reaxys 198/325 Yield

Conditions & References in neat (no solvent), byproducts: pyridine; on air; within a few min.; Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 7; (1933); p. 60 - 78 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O

N O

N N

N N

3

Cu 2+

6 O–

N

N N

6 O– H

3 Cu 2+

10

N

H

H

Rx-ID: 26647479 View in Reaxys 199/325 Yield

Conditions & References With ammonia, dry gaseous NH3; at ambient temp.;

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

61/96

2016-04-10 14:47:02

Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 7; (1933); p. 60 - 78 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O

N O

N N

N N

N

6

N N

O–

6 O– H

3 Cu 2+

3 Cu 2+

12

N

H

H

Rx-ID: 26647480 View in Reaxys 200/325 Yield

Conditions & References With ammonia, dry gaseous NH3; at -2 to -4 °C; Ripan, R.; Buletinul Societatii de Stiinte din Cluj; vol. 7; (1933); p. 60 - 78 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

3 K+ Cl 3Cl RhCl Cl Cl (v6)

O

H 2N

HO

Cl

O

6

NH 2

H 2N 3 NH –

3 Cl – 4

H O

H

4 – OH Rh 3+ 9 NH 2N 2

Rx-ID: 26695885 View in Reaxys 201/325 Yield

Conditions & References in not given, excess of hydrazine salt, pH 8 Cambi, L.; Paglia, E. D.; Bargigia, G.; Atti. Accad. Nazl. Lincei Rend. Classe Sci. Fis. Mat. Nazt.; vol. 30; (1961); p.

636 - 643 ; (from Gmelin) View in Reaxys vol. Rh: SVol.B2; 1.1.4.4, page 62 - 62 ; (from Gmelin) View in Reaxys

2 O–

NH 2 2 O–

4 Ni 2+ H 2N

O

O

Ni 2+

Rx-ID: 26737319 View in Reaxys 202/325 Yield

Conditions & References in ethanol, prepn. from Ni(CH2CNCO2)2 and excess benzylamine in alc. soln.;; pptn., washing with alc., drying on air; Ablov, A.; Bull. Soc. Chim. France (5); vol. 1; (1934); p. 1489 - 1494 ; (from Gmelin) View in Reaxys in ethanol, prepn. from Ni(CH2CNCO2)2 and excess benzylamine in alc. soln.;; pptn., washing with alc., drying on air; vol. Ni: MVol.C1; 57, page 140 - 141 ; (from Gmelin) View in Reaxys

HO

O O

Sc( 3+)

3 O–

Sc 3+

Rx-ID: 26786404 View in Reaxys 203/325 Yield

Conditions & References in not given, 35-fold excess of phenylacetic acid, pH 4 to 5; dried at 120°C

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

62/96

2016-04-10 14:47:02

Liu, Ch.; Wang, Sh.; Liang, Sh.; Huaxue Xuebao (Zengkan); (1981); p. 105 - 108; C.A.; vol. 98; (1983); p. 190845 ; (from Gmelin) View in Reaxys in not given, 35-fold excess of phenylacetic acid, pH 4 to 5; dried at 120°C vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys H

3

O

O

N+

3

O–

O– Sc 3+

O

O–

Sc 3+

H H

H

N+

HH

HO( 1-)

O

2 O–

Rx-ID: 26810549 View in Reaxys 204/325 Yield

Conditions & References in not given, moderately hot dild. soln. of educts, boiling; washed out with warm water from the beaker Crookes, W.; Chem. News J. Ind. Sci.; vol. 98; (1908); p. 307 - 309 ; (from Gmelin) View in Reaxys in not given, moderately hot dild. soln. of educts, boiling; washed out with warm water from the beaker vol. Sc: MVol.D5; 1.1.4, page 67 - 69 ; (from Gmelin) View in Reaxys

O

HO

HO O–

O

O K+

Rx-ID: 66201 View in Reaxys 205/325 Yield

Conditions & References With potassium hydroxide, ethanol Smith; Speakman; Transactions of the Faraday Society; vol. 44; (1948); p. 1031,1032 View in Reaxys

2H

O O–

Na +

2H

O

Na + O–

Rx-ID: 2428694 View in Reaxys 206/325 Yield

Conditions & References With sodium hydroxide, water-d2, pH=13 Maas, Wilfrid P. M.; Veelen, Peter A. van; Nibbering, Nico M. M.; Organic Mass Spectrometry; vol. 24; (1989); p.

546 - 558 View in Reaxys

O

HO

sodium carbonate

O

HO 2

O–

O Na +

Rx-ID: 8474962 View in Reaxys 207/325 Yield

Conditions & References With benzene Crawford; Journal of the Chemical Society; (1941); p. 259,262

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

63/96

2016-04-10 14:47:02

View in Reaxys 2H

O N

N

HO 2H

O

Rx-ID: 9456999 View in Reaxys 208/325 Yield

Conditions & References in 1,4-dioxane, water, Time= 0.75h Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

N

HO

14C

14C

O

Rx-ID: 10399109 View in Reaxys 209/325 Yield

Conditions & References With hydrogenchloride, propionic acid, Time= 0.05h, microwave irradiation Mathew; Ravi; Unny; Sivaprasad; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 8; (2006); p. 699 - 705 View in Reaxys O

2H 2H

O

HO

O

Rx-ID: 18866149 View in Reaxys 210/325 Yield

Conditions & References Reaction Steps: 2 1: LiAlD4 2: 1) SOCl2, 2) Mg With thionyl chloride, lithium aluminium deuteride, magnesium Gessner, Uwe; Heesing, Albert; Chemische Berichte; vol. 118; nb. 7; (1985); p. 2593 - 2606 View in Reaxys

N

Co 2+O

S

O–

O–

O O–

O–

O

H H

2

2 O

N+ HH

N Co 2+

2

H O

H

Rx-ID: 26301248 View in Reaxys 211/325 Yield

Conditions & References in water, formation at addition of pyridine and CoSO4 to an aq. NH4-phenylacetate-solution; seperation of the crystals after 2 h;; washing with pyridine-containing water; drying in air; Costachescu, N.; Ablov, A.; Annales Scientifiques de l'Universite de Jassy, Section 1: Mathematiques, Physique, Chimie; vol. 25; (1939); p. 384 - 394 ; (from Gmelin) View in Reaxys in water, formation at addition of pyridine and CoSO4 to an aq. NH4-phenylacetate-solution; seperation of the crystals after 2 h;; washing with pyridine-containing water; drying in air; vol. Co: SVol.B1; 35, page 73 - 75 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

64/96

2016-04-10 14:47:02

-2

O

(v1)

Na +

O–

Cu 2+

O

O

O

(v1)

2

O

Cu 2+

O–

S O

Rx-ID: 26324322 View in Reaxys 212/325 Yield

Conditions & References in water, precipitate; washed with H2O; Ablov, A.; Ann. Sci. Univ. Jassy; vol. 17; (1931); p. 173 - 187 View in Reaxys vol. Cu: MVol.B2; 48, page 724 - 726 ; (from Gmelin) View in Reaxys

O– NH 2 NH 2 O

4 2 O–

Ni 2+

HN H 2N

H

3

O

O

H H Ni 2+

H

Rx-ID: 26713769 View in Reaxys 213/325 Yield

Conditions & References in ethanol, prepn. from alc. solns. of Ni(C6H5CH2CO2)2 and phenylhydrazine;; pptn., washing with alc. and drying in air; Ablov, A.; Bull. Soc. Chim. France (5); vol. 1; (1934); p. 1489 - 1494 View in Reaxys vol. Ni: MVol.C1; 59, page 144 - 145 ; (from Gmelin) View in Reaxys OH Br

2

O–

N

Mn2+

N

OH

O

Br

O–

O

N

Br

O–

O

–O

3

O–

N

–O

3

O–

Br

Br 3 Mn2+

Mn3+

N

N

Br

Mn3+

Rx-ID: 27223788 View in Reaxys 214/325 Yield

Conditions & References

6%

in ethanol, reflux (2.5 h); filtration, concn., pptn. upon addn. to Et2O, washing (Et2O), drying (vac.); elem. anal.

Hulme, Charlotte E.; Watkinson, Michael; Haynes, Michaela; Pritchard, Robin G.; McAuliffe, Charles A.; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 11; (1997); p. 1805 1814 ; (from Gmelin) View in Reaxys

H HO

O

NH 2 NH 2Cl

H

O H 2N

O

OH NH 2

OH

Rx-ID: 33014873 View in Reaxys 215/325 Yield

Conditions & References Reaction Steps: 2 1: water; dimethyl sulfoxide / 2 h / 20 °C / Industry scale 2: water; dimethyl sulfoxide / 0.5 h / 33 - 37 °C / Industry scale in water, dimethyl sulfoxide Patent; OCERA THERAPEUTICS, INC.; ANDERSON, Keith, H.; BEHLING, Jim; DOUGAN, Christine, Henderson; WATT, Stephen, William; MANINI, Peter; FIGINI, Attilia; WO2012/48043; (2012); (A1) English

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

65/96

2016-04-10 14:47:02

View in Reaxys O HO

H 2N

O

O OH

H 2N

O

Rx-ID: 33504025 View in Reaxys 216/325 Yield

Conditions & References in ethanol, Heating Chaudhari, Sachin Rama; Suryaprakash; Journal of Molecular Structure; vol. 1016; (2012); p. 163 - 168 View in Reaxys

O

O

O

N

N

O O–

O– O 13C

13C

Cl

OH

O

Cl

O

2H

N+

N+

Rx-ID: 35714302 View in Reaxys 217/325 Yield

Conditions & References With methanol-d1 Koeppe, Benjamin; Guo, Jing; Tolstoy, Peter M.; Denisov, Gleb S.; Limbach, Hans-Heinrich; Journal of the American Chemical Society; vol. 135; nb. 20; (2013); p. 7553 - 7566 View in Reaxys

HO

O

HO

N

H N

N

2 O

O

Rx-ID: 66125 View in Reaxys 218/325 Yield

Conditions & References With ethanol Knott; Journal of the Chemical Society; (1945); p. 686,687,688 View in Reaxys

O

HO

N

HO

N

H N

2 O

O

Rx-ID: 796077 View in Reaxys 219/325 Yield

Conditions & References With ethanol Knott; Journal of the Chemical Society; (1945); p. 686,687,688 View in Reaxys

2H

O

O

2H

HO

2H 2

H

HO

O

Rx-ID: 2000449 View in Reaxys 220/325 Yield

Conditions & References With thionyl chloride, magnesium, Multistep reaction

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

66/96

2016-04-10 14:47:02

Gessner, Uwe; Heesing, Albert; Chemische Berichte; vol. 118; nb. 7; (1985); p. 2593 - 2606 View in Reaxys 2H

2

H

O

O

HO

Cl

O

Rx-ID: 2000573 View in Reaxys 221/325 Yield

Conditions & References With magnesium, 1.) Et2O, reflux, 30 min, 2.) room temperature, Yield given. Multistep reaction Bakke, Jan M.; Chadwick, Derek J.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 42; nb. 4; (1988); p. 223 - 230 View in Reaxys

HO

N 2H

O

2H

Rx-ID: 2036304 View in Reaxys 222/325 Yield

Conditions & References hydrolysis Chao, Herbert S.-I.; Berchtold, Glenn A.; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1191 - 1194 View in Reaxys

–O

O O

OH

O

Rx-ID: 3959237 View in Reaxys 223/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

O O

–O

O

HO

Rx-ID: 3959394 View in Reaxys 224/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

O

–O

O HO

O

Rx-ID: 3963212 View in Reaxys 225/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

67/96

2016-04-10 14:47:02

Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

–O

O

HO

O

O

Rx-ID: 3964150 View in Reaxys 226/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

–O

O O

O

HO

Rx-ID: 3964303 View in Reaxys 227/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

F

F

F

O F

F

HO

–O

F

O

O

Rx-ID: 3964494 View in Reaxys 228/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

O

OH

O

–O

O

Rx-ID: 3984702 View in Reaxys 229/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

68/96

2016-04-10 14:47:02

F F

F

O F F

F

–O

F

F F

F O

F

O

OH

F

Rx-ID: 4002123 View in Reaxys 230/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

–O

O O

HO

O

Rx-ID: 4030145 View in Reaxys 231/325 Yield

Conditions & References With potassium chloride, hydroxide in 1,4-dioxane, water, T= 25 °C , also for the pig liver esterase catalysed hydrolysis, Rate constant Barton, Patrick; Laws, Andrew P.; Page, Michael I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1994); p. 2021 - 2030 View in Reaxys

O 13C

N

N

H

13C 2

HO O

HO

13C

O

Rx-ID: 9483905 View in Reaxys 232/325 Yield

Conditions & References in 1,4-dioxane, water, Time= 0.75h, Irradiation, Title compound not separated from byproducts Haiss, Peter; Zeller, Klaus-Peter; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 6; (2003); p. 595 - 605 View in Reaxys

N

(v2)(v3) (v5) (v2) (v3) –O OMo2+–O

O

4

2

O–

N

– 2+ – O OMoO O (v3)(v2) (v5) (v3)(v2)

O (v1)

2+Mo

Mo2+

(v1)

Rx-ID: 27359681 View in Reaxys 233/325 Yield

Conditions & References in neat (no solvent), (Ar); heating (reflux until dissolved), cooling (room temp.); washing (dry ethanol), drying (vacuum); elem. anal.

Akhmedov; Khasaev; Tsivadze; Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya; vol. 23; nb. 8; (1997); p. 576 - 579 ; (from Gmelin) View in Reaxys

N

(v2) (v3) (v5)2+ (v2) (v3) –O OMo –O

O

2

4

O–

N

– 2+ – O OMoO O (v3)(v2) (v5) (v3)(v2)

O (v1)

2+Mo

Mo2+

(v1)

Rx-ID: 27359682 View in Reaxys 234/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

69/96

2016-04-10 14:47:02

Yield

Conditions & References in neat (no solvent), (Ar); heating (reflux until dissolved), cooling (room temp.); washing (dry ethanol), drying (vacuum); elem. anal.

Akhmedov; Khasaev; Tsivadze; Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya; vol. 23; nb. 8; (1997); p. 576 - 579 ; (from Gmelin) View in Reaxys

N

(v2) – (v3)

(v5) (v2) (v3)

4

2+– O OMoO O

2 O– N

– 2+ – O OMoO O

(v3)(v2)

O

(v5) (v3)(v2) 2+Mo

(v1)

Mo2+

(v1)

Rx-ID: 27359683 View in Reaxys 235/325 Yield

Conditions & References in neat (no solvent), (Ar); heating (reflux until dissolved), cooling (room temp.); washing (dry ethanol), drying (vacuum); elem. anal.

Akhmedov; Khasaev; Tsivadze; Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya; vol. 23; nb. 8; (1997); p. 576 - 579 ; (from Gmelin) View in Reaxys

N (v2) (v3) (v5)2+ (v2) (v3) –O OMo –O

2

O

– 2+ – O OMoO O

(v3)(v2)

(v5) (v3)(v2)

4

O– O

N (v1)

2+Mo

Mo2+ (v1)

Rx-ID: 27359684 View in Reaxys 236/325 Yield

Conditions & References in neat (no solvent), (Ar); heating (reflux until dissolved), cooling (room temp.); washing (dry ethanol), drying (vacuum); elem. anal.

Akhmedov; Khasaev; Tsivadze; Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya; vol. 23; nb. 8; (1997); p. 576 - 579 ; (from Gmelin) View in Reaxys

HO O

(v4) Si CH –2 (v4) – C Si (v6) H 23+ (v2) – (v4) Re (v4) – (v2) Si CH Cl–2 –Cl H 2C Si 3+Re (v6) Re 3+ (v6) Cl – (v4) –H C (v2) – H C Si 2 (v4) 2

3

Cl –

O–

6 O Re 3( 9+)

Si

Rx-ID: 27493670 View in Reaxys 237/325 Yield

Conditions & References in toluene, inert atmosphere; addn. of large excess of phenylacetic acid to Re-complex, refluxing (20 h, pptn.); filtration, washing (light petroleum), extn. (CH2Cl2), filtration, concn., cooling to -78°C, recrystn. (hot toluene); elem. anal.

Edwards, Peter G.; Felix, Franz; Mertis, Konstantinos; Wilkinson, Geoffrey; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1979); p. 361 - 366 ; (from Gmelin) View in Reaxys

HO O

(v4) Si CH –2 (v4) – C Si (v6) H 23+ (v2) – (v4) Re (v4) – (v2) Si CH Cl–2 –Cl H 2C Si 3+Re (v6) Re 3+ (v6) Cl – (v4) –H C (v2) – H C Si 2 (v4) 2

3

Si 3

Si

3 CH –2

O– O

Cl –

Re 3( 9+)

Rx-ID: 27493671 View in Reaxys 238/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

70/96

2016-04-10 14:47:02

Yield

Conditions & References in Petroleum ether, inert atmosphere; addn. of large excess of phenylacetic acid to Re-complex, stirring (2 h); cooling to -78°C, filtration, washing (cold light petroleum), recrystn. (hot light petroleum or toluene), recrystn. (hot THF); elem. anal.

Edwards, Peter G.; Felix, Franz; Mertis, Konstantinos; Wilkinson, Geoffrey; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1979); p. 361 - 366 ; (from Gmelin) View in Reaxys

O

HO O

N H

N+

HN

OH –

O O– O

N H

N+

HN

Rx-ID: 32493478 View in Reaxys 239/325 Yield

Conditions & References in methanol, water, Time= 1h Dutta, Sounak; Shome, Anshupriya; Kar, Tanmoy; Das, Prasanta Kumar; Langmuir; vol. 27; nb. 8; (2011); p.

5000 - 5008 View in Reaxys

O

O O–

Na +

2

Cl 2Zn

Zn 2+

O–

Rx-ID: 36525425 View in Reaxys 240/325 Yield 8.59 g

Conditions & References in water, pH= 3.0 Cui, Xiaoneng; Zhao, Jianzhang; Yang, Pei; Sun, Jifu; Chemical Communications; vol. 49; nb. 87; (2013); p.

10221 - 10223 View in Reaxys

HO

H 2N

H

O

O

O–

–O

NH 2

O

2

H 2N 2 NH 2

Zn 2+

H

O

O–

Zn 2+

Rx-ID: 26763309 View in Reaxys 241/325 Yield >99

Conditions & References in ethanol, byproducts: CO2, H2O; slow addn. of the metal carbonate to an alcoholic soln. of phenylacetic acid with stirring and warming, filtn. and slow addn. of N2H4*H2O to the metal phenylacetate; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys

HO

O–

–O

O

O Cd 2+ O–

H 2N

H O

NH 2

2

Cd 2+ O

H

H 2N 2 NH 2

Rx-ID: 26800252 View in Reaxys 242/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

71/96

2016-04-10 14:47:02

Yield

Conditions & References

>99

in ethanol, byproducts: CO2, H2O; slow addn. of the metal carbonate to an alcoholic soln. of phenylacetic acid with stirring and warming, filtn. and slow addn. of N2H4*H2O to the metal phenylacetate; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys

HO

–

O–

O–

O

Ni 2+

O

O

H 2N

H O

2

NH 2

H 2N 2 NH 2 O

H

Ni 2+

Rx-ID: 26800296 View in Reaxys 243/325 Yield

Conditions & References

>99

in ethanol, byproducts: CO2, H2O; slow addn. of the metal carbonate to an alcoholic soln. of phenylacetic acid with stirring and warming, filtn. and slow addn. of N2H4*H2O to the metal phenylacetate; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys O–

HO

H 2N

H

O

O

O–

NH 2

2

Co

H

O

O–

O

Co 2+

2+

H 2N 2 NH 2

Rx-ID: 26800297 View in Reaxys 244/325 Yield

Conditions & References

>99

in ethanol, byproducts: CO2, H2O; slow addn. of the metal carbonate to an alcoholic soln. of phenylacetic acid with stirring and warming, filtn. and slow addn. of N2H4*H2O to the metal phenylacetate; filtn., washing with alcohol and ether and drying over P4O10 (vac.); elem. anal.

Jiji, E. R.; Aravindakshan, K. K.; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 23; (1993); p. 119 - 132 ; (from Gmelin) View in Reaxys

H

-1

O–

N

O

H

9

O Na +

O–

7 N

Na +

8

Cl 2Co

Co 2+

O–

OH

N 2

O– O

Na +

H 2O2( 2-)

Rx-ID: 27136162 View in Reaxys 245/325 Yield

Conditions & References in methanol, CoCl2*xH2O and Na-salts were stirred in MeOH for 24 h; filtered, evapd. to dryness under reduced pressure, dried in vacuo overnight, extd. with MeCN, filtered, allowed to stand for 14 months Brechin, Euan K.; Graham, Alasdair; Parkin, Andrew; Parsons, Simon; Seddon, Annela M.; Winpenny, Richard E. P.; Journal of the Chemical Society, Dalton Transactions; nb. 19; (2000); p. 3242 - 3252 ; (from Gmelin) View in Reaxys Cl –O

HO O

O

Rx-ID: 5315882 View in Reaxys 246/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

72/96

2016-04-10 14:47:02

Yield

Conditions & References With methanogenic bacteria, yeast extract, Time= 6574.5h, T= 30 °C , Microbiological reaction, Dehalogenation, Product distribution, Further Variations: Reagents Genthner, Barbara R. Sharak; Biodegradation; vol. 10; nb. 1; (1999); p. 27 - 34 View in Reaxys

O

O

HO

Na +

O–

O

HO 2

O–

O Na +

Rx-ID: 66153 View in Reaxys 247/325 Yield

Conditions & References Bakunin; Peccerillo; Gazzetta Chimica Italiana; vol. 65; (1935); p. 1145,1149 View in Reaxys Vitale; Gazzetta Chimica Italiana; vol. 66; (1936); p. 566,567 View in Reaxys 2H

2H

2H

2H

HO

Br

O

Rx-ID: 2125279 View in Reaxys 248/325 Yield

Conditions & References Yield given. Multistep reaction Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 18; (1982); p. 317 - 324; Zhurnal Organicheskoi Khimii; vol. 18; nb. 2; (1982); p. 365 - 373 View in Reaxys

3

C H2 Pr

O– H O

O

H

3

O– C H2

Pr3+ O

3+

Rx-ID: 27529392 View in Reaxys 249/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 120°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

3

C H2

O– H O

O

H

3

O– C H2

Nd 3+ O

Nd 3+

Rx-ID: 27529395 View in Reaxys 250/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 120°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

73/96

2016-04-10 14:47:02

O–

3

Ce 3+

C H2

O–

3

O

C H2

H O

Ce 3+ O

H

Rx-ID: 27529403 View in Reaxys 251/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 110-120°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O–

3

H O

H

3

O

O– C H2

Ho 3+ O

Ho 3+

Rx-ID: 27531011 View in Reaxys 252/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 110°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O–

3

H O

H

3

O

O– C H2

Yb3+ O

Yb3+

Rx-ID: 27531012 View in Reaxys 253/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 85°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O– Er3+

3

3 O

O– C H2

Er3+ O

H O

H

Rx-ID: 27531015 View in Reaxys 254/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 130°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

74/96

2016-04-10 14:47:02

O H

3

O

O–

H

3

O– La 3+ O

La 3+

Rx-ID: 27719612 View in Reaxys 255/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 110°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O–

3

H O

H

3

O

O– Sm3+ O

Sm3+

Rx-ID: 27719613 View in Reaxys 256/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 120°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O–

3

H O

H

3

O

O– Tb 3+ O

Tb 3+

Rx-ID: 27719615 View in Reaxys 257/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 110°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O–

3

H O

H

3

O Tm3+

O– Tm3+ O

Rx-ID: 27719617 View in Reaxys 258/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 97°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

75/96

2016-04-10 14:47:02

O–

3

H O

H

3

O– Lu 3+

O

O

Lu 3+

Rx-ID: 27719620 View in Reaxys 259/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 80°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O– Eu3+

3

3 O

O– Eu3+ O

H O

H

Rx-ID: 27719624 View in Reaxys 260/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 110°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O– Dy 3+

3

3 O

O– Dy 3+ O

H O

H

Rx-ID: 27719626 View in Reaxys 261/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 85°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

O– Gd 3+

3

3

O

O– Gd 3+ O

H O

H

Rx-ID: 27719628 View in Reaxys 262/325 Yield

Conditions & References byproducts: H2O; isothermal heating at 105°C; monitoring by thermogravimetric and differential thermal anal.,; X-ray diffraction Pirkes, S. B.; Krasovskaya, T. A.; Kurbatova, S. V.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 23; (1978); p. 217 - 219; Zhurnal Neorganicheskoi Khimii; vol. 23; (1978); p. 390 393 ; (from Gmelin) View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

76/96

2016-04-10 14:47:02

H N

N

HO

HO

H N

N

2 O

O

Rx-ID: 672493 View in Reaxys 263/325 Yield

Conditions & References Knott; Journal of the Chemical Society; (1945); p. 686,687,688 View in Reaxys O O

O

Na +

O–

O

O

Rx-ID: 9080767 View in Reaxys 264/325 Yield

Conditions & References With N-hexadecyl-N,N,N-trimethylammonium bromide, sodium carbonate, triethylamine, Time= 12h, T= 20 °C , Photolysis, Product distribution, Further Variations: Reagents, Solvents, time periods Ruzicka, Radovan; Zabadal, Miroslav; Klan, Petr; Synthetic Communications; vol. 32; nb. 16; (2002); p. 2581 2590 View in Reaxys

HO

–O

O–

H

Ni 2+

O

O

O

H

O

2

4H O 2

O–

Ni 2+

Rx-ID: 36932819 View in Reaxys 265/325 Yield

Conditions & References Heating Ghosh, Aloke Kumar; Shatruk, Michael; Bertolasi, Valerio; Pramanik, Kausikisankar; Ray, Debashis; Inorganic Chemistry; vol. 52; nb. 24; (2013); p. 13894 - 13903 View in Reaxys

HO

O

O– O

H

Mn2+ O

O–

O

2

H

O–

H O

H

Mn2+

Rx-ID: 38677183 View in Reaxys 266/325 Yield

Conditions & References Time= 0.166667 - 0.25h, Heating Seth, Piya; Figuerola, Albert; Jover, Jesus; Ruiz, Eliseo; Ghosh, Ashutosh; Inorganic Chemistry; vol. 53; nb.

17; (2014); p. 9296 - 9305 View in Reaxys

N O

HO

N O

N

N

(v2)

N O–

N+

N

N

N

N

NH

N

Rx-ID: 1623517 View in Reaxys 267/325 Yield

Conditions & References in N,N-dimethyl-formamide, Ambient temperature, Equilibrium constant Jaworski, Jan S.; Krawczyk, Irena; Monatshefte fuer Chemie; vol. 123; nb. 1/2; (1992); p. 43 - 50

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

77/96

2016-04-10 14:47:02

View in Reaxys

N+

N+

N+

N+

O

–O

O–

O

N+

N+

N+

N+

Rx-ID: 2217449 View in Reaxys 268/325 Yield

Conditions & References in water, Ambient temperature, study of synthetic host-guest complexes; ΔG, Thermodynamic data Schneider, Hans-Joerg; Blatter, Thomas; Simova, Svetlana; Theis, Isolde; Journal of the Chemical Society, Chemical Communications; nb. 9; (1989); p. 580 - 581 View in Reaxys

HO

H H

O

H H

B– PH

–O

H

(v5)

P

B

H

H

O

H

Rx-ID: 28922769 View in Reaxys 269/325 Yield

Conditions & References T= 57.84 °C , Gas phase, Equilibrium constant Hurtado, Marcela; Yanez, Manuel; Herrero, Rebeca; Guerrero, Andres; Juan Z. Davalos; Jose-Luis, M. Abboud; Khater, Brahim; Guillemin, Jean-Claude; Chemistry - A European Journal; vol. 15; nb. 18; (2009); p. 4622 4629 View in Reaxys

O

O

O

O–

(v1)

CH 2

CH +2

Rx-ID: 3223788 View in Reaxys 270/325 Yield

Conditions & References ΔG0, Thermodynamic data Yamaguchi; Kuriyama; Sakuragi; Tokumaru; Tetrahedron Letters; vol. 33; nb. 38; (1992); p. 5529 - 5532 View in Reaxys

HO

Na

OH O

H 2N 2

O O–

Na +

Rx-ID: 587177 View in Reaxys 271/325 Yield

Conditions & References Schlenk; Holtz; Chemische Berichte; vol. 50; (1917); p. 271 View in Reaxys Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

78/96

2016-04-10 14:47:02

O

O

sodium

O

O

O

Na +

O–

hydrogen Rx-ID: 6214857 View in Reaxys 272/325

Yield

Conditions & References Hodgkinson; Journal of the Chemical Society; vol. 37; (1880); p. 482 View in Reaxys

O

sodium

O

O

O

O

Na +

O–

Rx-ID: 7442222 View in Reaxys 273/325 Yield

Conditions & References Hodgkinson; Journal of the Chemical Society; vol. 37; (1880); p. 482 View in Reaxys

O O–

K+

Rx-ID: 25030005 View in Reaxys 274/325 Yield 86%

Conditions & References 2 : EXAMPLE 2 The carbonyltion was run for 90 minutes during which time 63 ml of the KOH solution, and 21 ml of the PPh3 solution were added.

An 86percent overall yield of potassium phenylacetate was obtained.

Patent; Stauffer Chemical Company; US4713484; (1987); (A1) English View in Reaxys C.1 : COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 Into the same reactor described in Example 1 was placed 53.7 mg PdCl2 (PPh3)2, 0.285 g PPh3, and 17.45 g KOH (87.8percent).

Under a N2 purge, deoxygenated benzyl chloride, 17.86 g methanol, 81.7 g, and diisopropyl ethyl amine, 0.23 g, were added.

The reactor was flushed with high purity CO, pressurized to 15 psig, and heating begun with stirring.

At 79° the pressure was increased from 26 to 45 psig and maintained at this value during the reaction.

After 1 hr. 40 min. under these conditions, the heating has stopped and the reactor vented when cool.

Analysis of the reaction product revealed that only at 6percent conversion to potassium phenylacetate was obtained.

Patent; Stauffer Chemical Company; US4713484; (1987); (A1) English View in Reaxys

O

2-methylthioethylanine

H 2N

S

OH

Rx-ID: 25243304 View in Reaxys 275/325 Yield 13.6 g (75%), 92%

Conditions & References 12 : EXAMPLE 12 After cooling, the mixture is diluted with 200 cc of ether and then filtered to remove therefrom the mineral salts.

The filtrate is concentrated and the resulting oily residue is fractionated.

The fraction distilling at 42°C under 16 mm Hg, is recovered and yields 13.6 g (75percent) of 2-methylthioethylanine which are added, in a solution of ether (300 cc), to a solution of phenyl-acetic acid (0.15 mol) in the same solvent.

The salt formed crystallizes, in proportion to the addition, in the form of white needles (33.5 g) which are purified by crystallization in ethyl acetate.

Yield = 92percent.

Fusion point: 92°- 94°C.

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

79/96

2016-04-10 14:47:02

Patent; L'Oreal; US3976781; (1976); (A1) English View in Reaxys

O H 2N

S

2 -methylthioethylanine

OH

Rx-ID: 25301678 View in Reaxys 276/325 Yield

Conditions & References

13.6 g (75%), 92%

12 : Example 12 After cooling, the mixture is diluted with 200 cc of ether and then filtered to remove therefrom the mineral salts.

The filtrate is concentrated and the resulting oily residue is fractionated.

The fraction distilling at 42° C under 16 mm Hg, is recovered and yields 13.6 g (75percent) of 2 -methylthioethylanine which are added, in a solution of ether (300 cc), to a solution of phenyl-acetic acid (0.15 mol) in the same solvent.

The salt formed crystallizes, in proportion to the addition, in the form of white needles (33.5 g) which are purified by crystallization in ethyl acetate.

Yield = 92percent.

Fusion point: 92°-94° C. Patent; L'Oreal; US4035492; (1977); (A1) English View in Reaxys

O O OH

O N

Rx-ID: 23980108 View in Reaxys 277/325 Yield

Conditions & References Compounds illustrative of the scope of this invention include the following: 3-(p-isopropoxyphenxoy)-3-phenylpropylamine methanesulfonate; ...

N-methyl 3-(p-tolyloxy)-3-phenylpropylamine sulfate; N,N-dimethyl 3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate; 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate; N-methyl-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate; N,N-dimethyl 3-(o-isopropoxyphenoxy)-3-phenyl-propylamine phenylacetate; N,N-dimethyl 3-(o-)bromophenoxy)-3-phenyl-propylamine beta-phenylpropionate; N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine propiolate; Patent; Ramot University Authority for Applied Research And Industrial Development Ltd.; US2003/87964; (2003); (A1) English View in Reaxys , wherein said 3-aryloxy-3-phenylpropylamine is selected from the group consisting of 3-(p-isopropoxyphenxoy)-3-phenylpropylamine methanesulfonate, ...

N-methyl 3-(p-tolyloxy)-3-phenylpropylamine sulfate, N,N-dimethyl 3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate, 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate, N-methyl-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate, N,N-dimethyl 3-(o-isopropoxyphenoxy)-3-phenyl-propylamine phenylacetate, N,N-dimethyl 3-(o-)bromophenoxy)-3-phenyl-propylamine beta-phenylpropionate, N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine propiolate, N-methyl 3-(3-n-propylphenoxy)-3-phenyl-propylamine decanoate, and ...

Patent; Ramot University Authority for Applied Research And Industrial Development Ltd.; US2003/87964; (2003); (A1) English

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

80/96

2016-04-10 14:47:02

View in Reaxys , wherein said at least one 3-aryloxy-3-phenylpropylamine is selected from the group consisting of 3-(p-isopropoxyphenxoy)-3-phenylpropylamine methanesulfonate, ...

N-methyl 3-(p-tolyloxy)-3-phenylpropylamine sulfate, N,N-dimethyl 3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate, 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate, N-methyl-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate, N,N-dimethyl 3-(o-isopropoxyphenoxy)-3-phenyl-propylamine phenylacetate, N,N-dimethyl 3-(o-)bromophenoxy)-3-phenyl-propylamine beta-phenylpropionate, N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine propiolate, N-methyl 3-(3-n-propylphenoxy)-3-phenyl-propylamine decanoate, and ...

Patent; Ramot University Authority for Applied Research And Industrial Development Ltd.; US2003/87964; (2003); (A1) English View in Reaxys Compounds illustrative of the scope of this invention include the following: 3-(p-isopropoxyphenxoy)-3-phenylpropylamine methanesulfonate; ...

N-methyl 3-(p-tolyloxy)-3-phenylpropylamine sulfate; N,N-dimethyl 3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate; 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate; N-methyl-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate; N,N-dimethyl 3-(o-isopropoxyphenoxy)-3-phenyl-propylaminephenylacetate; N,N-dimethyl 3-(o-)bromophenoxy)-3-phenyl-propylamine beta-phenylpropionate; N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine propiolate; Patent; Ramot University Authority for Applied Research And Industrial Development Ltd.; US2003/87964; (2003); (A1) English View in Reaxys Compounds illustrative of the scope of this invention include the following: ...

N-methyl 3-(p-tolyloxy)-3-phenylpropylamine sulfate N,N-dimethyl 3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate N-methyl 3-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate N,N-dimethyl 3-(o-isopropoxyphenoxy)-3-phenyl-propylamine phenylacetate N,N-dimethyl 3-(o-bromophenoxy)-3-phenyl-propylamine β-phenylpropionate N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine propiolate N-methyl 3-(3-n-propylphenoxy)-3-phenyl-propylamine decanoate Patent; Eli Lilly and Company; US4626549; (1986); (A1) English View in Reaxys Compounds illustrative of the scope of this invention include the following: ...

N-methyl 3-(p-tolyloxy)-3-phenylpropylamine sulfate N,N-dimethyl 3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate N-methyl 3-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate N,N-dimethyl 3-(o-isopropoxyphenoxy)-3-phenyl-propylamine phenylacetate N,N-dimethyl 3 -(o-)bromophenoxy)-3-phenyl-propylamine β-phenylpropionate N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine propiolate N-methyl 3-(3-n-propylphenoxy)-3-phenyl-propylamine decanoate Patent; Eli Lilly and Company; US4018895; (1977); (A1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

81/96

2016-04-10 14:47:02

HO

14

C O

Rx-ID: 7281474 View in Reaxys 278/325 Yield

Conditions & References K14CN, Benzylchlorid unter Phasentransferkatalyse Hayashi et al.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 15; (1978); p. 489,491 View in Reaxys 2-Phenyl-acrylsaeure, geschmolzenes KOH <Δ 2-3 Min.>, neben Ameisensaeure u. gasf. Produkten Bonner; Rewick; Journal of the American Chemical Society; vol. 84; (1962); p. 2334,2336 View in Reaxys Benzylmagnesiumbromid in Ether, Barium-<14C>-carbonat u. conc. H2SO4; Kuehlung (Trockeneis/A.) in N2 bei 10 Torr Sjoeberg; Undheim; Acta Chemica Scandinavica (1947-1973); vol. 17; (1963); p. 933 View in Reaxys (yield)80percent Sjoeberg; Undheim; Acta Chemica Scandinavica (1947-1973); vol. 17; (1963); p. 933 View in Reaxys Benzylmagnesiumbromid u. (14-C)-CO2 Oae; Furukawa; Bulletin of the Chemical Society of Japan; vol. 38; (1965); p. 62,63 View in Reaxys (yield)63percent Oae; Furukawa; Bulletin of the Chemical Society of Japan; vol. 38; (1965); p. 62,63 View in Reaxys Benzylmagnesiumchlorid, Ca14CO3 Roberts; Douglass; Journal of Organic Chemistry; vol. 28; (1963); p. 1225,1228 View in Reaxys (yield)82 percent Roberts; Douglass; Journal of Organic Chemistry; vol. 28; (1963); p. 1225,1228 View in Reaxys aus Benzyl-Mg-chlorid, (14C)O2 <aus Ba(14C)O3, HClO4>, Diethylether, (Kuehlung) Adema; Sixma; Recueil des Travaux Chimiques des Pays-Bas; vol. 81; (1962); p. 323,330 View in Reaxys Kaliumphenylacetat, 14CO2 Szabolcs et al.; Tetrahedron; vol. 30; (1974); p. 3647 View in Reaxys Benzyl-MgBr, Ba14CO3 Pines; Abramovici; Journal of Organic Chemistry; vol. 34; (1969); p. 70 View in Reaxys aus Benzyl-(14C)-cyanid Coke et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 1154 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

82/96

2016-04-10 14:47:02

2H 2H

HO

O

Rx-ID: 7282963 View in Reaxys 279/325 Yield

Conditions & References /BRN= 614465/ mit 1. NaOD/D2O, 2. Erhitzen, 3. H2O Givens et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 1896,1902 View in Reaxys α,α-Dideutero-benzylmagnesiumchlorid in Ae. mit CO2 <-20grad> Halevi et al.; Journal of the Chemical Society; (1963); p. 866,873 View in Reaxys Benzylcyanid, D2O Gruetzmacher; Organic Mass Spectrometry; vol. 3; (1970); p. 131,134 View in Reaxys Phenylessigsaeure, D2O Barnes; Scott; Canadian Journal of Chemistry; vol. 51; (1973); p. 411,418 View in Reaxys Na-phenylacetat, Na/D2O, Δ (S. 2803) Clifford; Waters; Journal of the Chemical Society; (1965); p. 2796,2802, 2804 View in Reaxys Phenylessigsaeure-Na-Salz, D2O-deuterierte Base bei 150grad Atkinson et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 498 View in Reaxys Phenylessigsaeure-K-Salz, D2O-deuterierte Base bei 150grad Atkinson et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 498 View in Reaxys (yield)66percent fuer beide Darstellungen Atkinson et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 498 View in Reaxys Phenylessigsaeure, D2O bei 100grad Koenig; Wolf; Journal of the American Chemical Society; vol. 91; (1969); p. 2569 View in Reaxys

N

HO O

Rx-ID: 24105100 View in Reaxys 280/325 Yield

Conditions & References 48.a : Prednisolone 17-n-butyrate 21-phenylacetate a) A solution of 500 mg of prednisolone 17-n-butyrate 21-mesylate (or an equimolar quantity of the analogous 21-pchlorobenzenesulfonate), 145 mg of phenylacetic acid and 112 mg of triethylamine (under these circumstances, intermediate formation of the triethylammoniumphenylacetate takes place) in 25 ml of dimethylformamide (or acetonitrile) is stirred at about 45° C. (oil bath) for 3 hours.

After this, the dimethylformamide, or acetonitrile, is distilled off in vacuo and the residue is treated with 30 ml of methylene chloride.

The organic phase is washed in succession with 1N aqueous hydrochloric acid and then 4 times with water.

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

83/96

2016-04-10 14:47:02

After chromatography in accordance with Example 46, and crystallization from diethyl ether, the abovementioned title compound is obtained, having the same parameters as given under Example 20 b).

Patent; STACHE, ULRICH; ALPERMANN, HANS-GEORG; DURCKHEIMER, WALTER; BOHN, MANFRED; US2002/103392; (2002); (A1) English View in Reaxys 40.a : Prednisolone 17-ethyl carbonate 21-phenylacetate a) A solution of 510 mg of prednisolone 17-ethyl carbonate 21-mesylate (or an equimolar quantity of the analogous 21p-chlorobenzene sulfonate), 145 mg of phenylacetic acid and 112 mg of triethylamine (under these circumstances, intermediary formation of the triethylammonium phenylacetate takes place) in 25 ml of dimethylformamide (or acetonitrile) are stirred at about 45° C. (oil bath) for 3 hours.

After that, the dimethylformamide or acetonitrile is distilled off in vacuo and the residue is treated with 30 ml of methylene chloride.

The organic phase is washed in succession with 1N aqueous hydrochloric acid and then 4 times with water.

Following chromatography in accordance with Example 2b, and crystallization from diethyl ether, the abovementioned title compound is obtained having the same parameters as given under Example 2b.

Patent; Hoechst Aktiengesellschaft; US5608093; (1997); (A1) English View in Reaxys

HN

N

O

HN

O

S OH NH

Rx-ID: 24259788 View in Reaxys 281/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

N-(2-ethoxy)phenyl-N'-(3-(1,4,5,6,7,8,9-heptahydroquinolizin-2-yl)-1H-indol-5-yl)thiourea N-(3-ethoxy)phenyl-N'-(3-(1-azabicyclo[5.4.0]undec-3-en-4-yl)-1H-indol-5-yl)thiourea N-(3-propoxy)phenyl-N'-(3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)-1H-indol-5-yl)thiourea N-(3-isopropoxy)phenyl-N'-(3-(1,4,5,6,7,8,9-heptahydroquinolizin-2-yl)-1H-indol-5-yl)thiourea N-(4-isopropoxy)phenyl-N'-(3-(1-azabicyclo[5.4.0]undec-3-en-4-yl)-1H-indol-5-yl)thiourea phenylacetate N-(3-butoxy)phenyl-N'-(3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)-1H-indol-5-yl)thiourea hydrochloride N-(2,3-dibromo)phenyl-N'-(3-(1,4,5,6,7,8,9-heptahydroquinolizin-2-yl)-1H-indol-5-yl)thiourea N-(2-bromo-3-iodo)phenyl-N'-(3-(1-azabicyclo[5.4.0]undec-3-en-4-yl)-1H-indol-5-yl)thiourea ...

Patent; Eli Lilly and Company; US5874427; (1999); (A1) English View in Reaxys The following group is illustrative of compounds contemplated within the scope of this invention: ...

N-(2-ethoxy)phenyl-N'-(3-(1,4,5,6,7,8,9-heptahydroquinolizin-2-yl)-1H-indol-5-yl)thiourea N-(3-ethoxy)phenyl-N'-(3-(1-azabicyclo [5.4.0]undec-3-en-4-yl)-1H-indol-5-yl)thiourea N-(3-propoxy)phenyl-N'-(3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)-1H-indol-5-yl)thiourea N- (3-isopropoxy)phenyl-N'-(3-(1,4,5,6,7,8,9-heptahydroquinolizin-2-yl)-1H-indol-5-yl)thiourea N-(4-isopropoxy)phenyl-N'-(3-(1-azabicyclo[5.4.0]undec-3-en-4-yl)-1H-indol-5-yl)thiourea phenylacetate N-(3-butoxy)phenyl-N'-(3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)-1H-indol-5-yl)thiourea hydrochloride N-(2,3-dibromo)phenyl-N'-(3-(1,4,5,6,7,8,9-heptahydroquinolizin-2-yl)-1H-indol-5-yl)thiourea N-(2-bromo-3-iodo)phenyl-N'-(3-(1-azabicyclo[5.4.0]undec-3-en-4-yl)-1H-indol-5-yl)thiourea ...

Patent; ELI LILLY AND COMPANY; EP875513; (1998); (A1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

84/96

2016-04-10 14:47:02

O

O

N

NH 2

OH

O

Rx-ID: 24110011 View in Reaxys 282/325 Yield

Conditions & References 1.3 : Step 3 Step 3 3-Amino-1-morpholin-4-yl-propan-1-one Compound with Phenylacetic Acid A reactor is charged with 3-amino-1-morpholin-4-yl-propan-1-one; hydrochloride (765 mmol). MeOH (380 mL) is added, and the mixture is stirred vigorously at room temperature for ca. 10 minutes. MtBE (380 mL) is added and the resulting slurry is cooled to -10C, where a 25percent (w/w) MeOH solution of NaOMe (765 mmol) is added slowly via addition funnel at such a rate as to maintain an internal temperature of ca. -10C. The resulting suspension is stirred vigorously under a N2 atmosphere as it is allowed to warm to 0° C. Solids are removed via filtration, rinsing with additional MtBE (50 mL).

Solvent is removed in vacuo to provide the free base as a crude oil that is taken up in MtBE (600 mL).

The mixture is cooled with vigorous agitation to ca. 0° C., where phenylacetic acid (765 mmol) is added slowly as a solution in MtBE (300 mL).

The reaction mixture is stirred an additional 10 minutes after complete addition, during which time the product precipitates out of solution.

The solids are collected via filtration, washed with additional MtBE (100 mL) and dried under vacuum at <40° C. to provide 3-amino-1-morpholin-4-yl-propan-1-one; compound with phenylacetic acid (191 g).

This material is carried on to subsequent steps without further purification, or optionally, it can be re-precipitated from MtBE. 1H NMR (400 MHz, DMSO) δ 2.55 (t, 2H, J=6.78), 2.86 (t, 2H, J=6.78) 3.62 (t, 2H), 3.42 (t, 2H), 6.22 (bs, 3H), 7.25-7.12 (m, 5H).

13C NMR (100 MHz, DMSO) δ 174.2, 169.0, 138.2, 129.2, 127.8, 125.5, 66.0, 45.2, 44.4, 41.4, 35.7, 31.6.

Patent; Butler, Donald Eugene; DeJong, Randall Lee; Nelson, Jade Douglas; Pamment, Michael Gerard; Stuk, Timothy Lee; US2002/133026; (2002); (A1) English View in Reaxys

Br OH 2

N

H

O

N HO

Rx-ID: 24403440 View in Reaxys 283/325 Yield

Conditions & References 39 : (3aS-cis)-7-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol, diphenylacetate EXAMPLE 39 (3aS-cis)-7-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol, diphenylacetate A stirred solution of 2.75 g of diphenylacetic acid and 2.10 g of 1,1'-carbonyldiimidazole in 150 ml of dry, degassed tetrahydrofuran was refluxed until evolution of carbon dioxide gas ceased.

The reaction solution was cooled to room temperature and 3.50 g of 7-bromo-(3aS-cis)-1,2,3,3a, 8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol was added under nitrogen.

The reaction solution was stirred overnight and then the solvent was removed, leaving an oily residue.

This was purified by chromatography over neutral alumina using dicholoromethane as eluent.

The fractions containing the product were combined and concentrated to an oil which crystallized from hexane.

This material was recrystallized three times from hexane to give 1.9 g of crystals of (3aS-cis)-7-bromo-1,2,3,3a,8,8ahexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol diphenylacetate, mp 93°-95° C. ANALYSIS: Calculated for C27 H27 BrN2 O2: 66.00percent C; 5.54percent H; 5.70percent N. Found: 66.01percent C; 5.68percent H; 5.64percent N. Patent; Hoechst-Roussel Pharmaceuticals Inc.; US5187165; (1993); (A1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

85/96

2016-04-10 14:47:02

HN

O

N

O

HN S

OH

NH

Rx-ID: 24638383 View in Reaxys 284/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

N-(2-ethoxy)phenyl-N'-(3-(1-(2-pentyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea N-(3-ethoxy)phenyl-N'-(3-(1-(2-hexyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea N-(3-propoxy)phenyl-N'-(3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea N-(3-isopropoxy)phenyl-N'-(3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea N-(4-isopropoxy)phenyl-N'-(3-(1-(3-pentyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea phenylacetate N-(3-butoxy)phenyl-N'-(3-(1-(2-pentyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea hydrochloride N-(2,3-dibromo)phenyl-N'-(3-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea N-(2-bromo-3-iodo)phenyl-N'-(3-1-(2-pentyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiourea ...

Patent; Eli Lilly and Company; US5708008; (1998); (A1) English View in Reaxys

NH N

HO O

N N O

Rx-ID: 24677210 View in Reaxys 285/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

5-(4-methoxybutoxy)carbonylamino(1-ethylpiperidin-4-yl)pyrrolo[3,2-b]pyridine 5-(propanoyl)amino-3-(1-neopentylpiperidin-4-yl)pyrrolo[3,2-b]pyridine mandelate 5-(2-methylpropanoyl)amino-3-(1-(3-pentyl)piperidin-4-yl)pyrrolo[3,2-b]pyridine 5-(2-methyl-4-butyn-1-oyl)amino-3-(1-(tert-butyl)piperidin-4-yl)pyrrolo[3,2-b]pyridine 5-(2-methylbutanoyl)-N-methylamino-3-(1-ethylpiperidin-4-yl)pyrrolo[3,2-b]pyridine phenylacetate 5-(hex-3-enoyl)amino-3-(1-propylpiperidin-4-yl)pyrrolo[3,2-b]pyridine 5-(cyclohexaneacetyl)amino-3-(1-isopropylpiperidin-4-yl)pyrrolo[3,2-b]pyridine 5-(cycloheptylcarbonyl)amino-3-(1-butylpiperidin-4-yl)pyrrolo[3,2-b]pyridine phenylpropionate ...

Patent; Eli Lilly and Company; US5817671; (1998); (A1) English View in Reaxys

HO O

HCl

Rx-ID: 24681954 View in Reaxys 286/325 Yield

Conditions & References II : Benzenacetic Acid Hydrochloride Benzenacetic Acid Hydrochloride A sodium hydride dispersion (3.3 g of a 60percent dispersion, 85 mmol) is washed with heptane (25 ml) under nitrogen, suspended in dry THF (80 ml), and stirred at room temperature.

A solution of diethyl phosphite (14.7 g, 110 mmol, Aldrich) in dry THF (20 ml) is added dropwise over thirty minutes as gas is evolved.

A solution of α-(benzoylamino)-4-[3-bromopropyl]benzeneacetic acid (8.0 g, 21.3 mmol) in dry THF (25 ml) is then added dropwise and the reaction stirred at room temperature overnight.

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

86/96

2016-04-10 14:47:02

The reaction is concentrated, taken up in a mixture of 250 ml ethyl acetate and 50 ml lN HCl and the ethyl acetate washed with 50 ml fresh lN HCl. The organics are extracted with lN NaOH (4*50 ml) and the product obtained by acidification of the stirred NaOH extracts with concentrated HCl. A solid forms which is filtered, washed with water, and air dried.

The material is purified by precipitation from a methanolic solution with diethyl ether.

A fine white solid was obtained (7.1 g, 77percent) with mp 167-8.

Patent; Warner-Lambert Company; US5175153; (1992); (A1) English View in Reaxys

2 Na +

–O

2 O

Rx-ID: 24687508 View in Reaxys 287/325 Yield

Conditions & References Additional aromatic compounds whose toxicities are reduced with bicarbonate are: Sodium Diphenylacetate Sodium 2,2'-Iminodibenzoate Sodium Phenoxyacetate Sodium Phenylpropionate Gemfibrozil Patent; Smith; Walton J.; US5173287; (1992); (A1) English View in Reaxys

N

O OH

O NH

Rx-ID: 24868280 View in Reaxys 288/325 Yield

Conditions & References Compounds illustrative of the scope of this invention include: ... (+-)-4-dimethylamino-6-propionoxy-1,3,4,5-tetrahydrobenz[c,d]indole hydrobromide (+-)-4-diethylamino-6-benzyloxy-1,3,4,5-tetrahydrobenz[c,d]indole tosylate (-)-4-diallylamino-6-hydroxy-1,3,4,5-tetrahydrobenz[c,d]indole malate (+-)-4-(di-n-propyl)amino-6-hydroxy-1,3,4,5-tetrahydrobenz[c,d]indole benzoate (-)-4-diethylamino-6-benzyloxy-1,3,4,5-tetrahydrobenz[c,d]indole phenylacetate (+)-4-dimethylamino-6-mesyloxy-1,3,4,5-tetrahydrobenz[c,d]indole 1,4-butyndioate (+-)-4-diallylamino-6-p-tosyloxy-1,3,4,5-tetrahydrobenz[c,d]indole hydrochloride (+-)-4-dimethylamino-6-p-toluyl-1,3,4,5-tetrahydrobenz[c,d]indole sulfate ...

Patent; Eli Lilly and Company; US4983622; (1991); (A1) English View in Reaxys

F F

F

O OH

F

N

Rx-ID: 24870044 View in Reaxys 289/325 Yield

Conditions & References The following compounds further illustrate compounds contemplated within the scope of the present invention:

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

87/96

2016-04-10 14:47:02

...

N,N-dimethyl-3-(3-ethylphenyl)-4-phenylbutanamine N,N-dimethyl-3-(2-methoxyphenyl)-4-phenylbutanamine N,N-dimethyl-3-phenyl-(2-methylphenyl)-butanaminium citrate N,N-dimethyl-3-phenyl-(3-n-propoxyphenyl)-butanaminium isobutyrate N,N-dimethyl-3-(2-trifluoromethylphenyl)-4(2-fluoro-5-methylphenyl)butanaminium phenylacetate N,N-dimethyl-3-(2,6-difluoro)-4-phenylbutanaminium maleate N,N-dimethyl-3-(3-bromophenyl)-4-phenylbutanaminium hydroxybenzoate N,N-dimethyl-3-(3-isopropoxyphenyl)-4-(3-methylphenyl)butanaminium hydrochloride ...

Patent; Eli Lilly and Company; US4996235; (1991); (A1) English View in Reaxys

NH O

N OH F

Rx-ID: 24939257 View in Reaxys 290/325 Yield

Conditions & References Compounds illustrative of the scope of this invention include: ... (+-)-4-dimethylamino-6-aminocarbonyl-1,3,4,5-tetrahydrobenz[c,d]indole hydrobromide (+-)-4-diethylamino-6-aminocarbonyl-1,3,4,5-tetrahydrobenz[c,d]indole tosylate (-)-4-diallylamino-6-aminocarbonyl-1,3,4,5-tetrahydrobenz[c,d]indole malate (+-)-4-(di-n-propyl)amino-6-bromo-1,3,4,5-tetrahydrobenz[c,d]indole benzoate (-)-4-diethylamino-6-fluoro-1,3,4,5-tetrahydrobenz[c,d]indole phenylacetate (+)-4-dimethylamino-6-chloro-1,3,4,5-tetrahydrobenz[c,d]indole 1,4-butyndioate (+-)-4-diallylamino-6-nitro-1,3,4,5-tetrahydrobenz[c,d]indole hydrochloride (+-)-4-dimethylamino-6-amino-1,3,4,5-tetrahydrobenz[c,d]indole sulfate ...

Patent; Eli Lilly and Company; US4576959; (1986); (A1) English View in Reaxys

O

HO O O

NH 2

Rx-ID: 25091081 View in Reaxys 291/325 Yield

Conditions & References Compounds illustrative of the scope of this invention include the following: ...

3-(2',4'-difluorophenoxy)-3-phenylpropylamine 2,4-dinitrobenzoate 3-(o-ethylphenoxy)-3-phenylpropylamine dihydrogen phosphate 3-(2'-chloro-4'-isopropylphenoxy)-3-phenyl-2-methylpropylamine maleate 3-(2'-allyl-4'-fluorophenoxy)-3-phenylpropylamine succinate 3-(o-isopropoxyphenoxy)-3-phenylpropylamine phenylacetate 3-(o-bromophenoxy)-3-phenylpropylamine-β-phenylpropionate 3-(p-iodophenoxy)-3-phenylpropylamine propiolate 3-(3' or n-propylphenoxy)-3-phenylpropylamine decanoate Patent; Eli Lilly and Company; US4313896; (1982); (A1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

88/96

2016-04-10 14:47:02

O HO

NH

NH 2

O N H

Rx-ID: 25471960 View in Reaxys 292/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

N-pentyl-N'-(4-(2-(1-isopropyl-1H-pyrazol-4-yl)ethyl)aminomethylcyclohepta[7,6-b]indol-7-yl)urea caproate N-(3-chloro)phenyl-N'-(4-(dipropyl)aminomethylcyclohepta[7,6-b]indol-7-yl)urea (-)-N-(4-bromo)phenyl-N'-(4-((sec-butyl)aminomethylcyclohepta[7,6-b]indol-7-yl)urea N-hexyl-N'-(4-aminomethylcyclohepta[7,6-b]indol-7-yl)urea 6-(acetyl)amino-3-amino-1,2,3,4-tetrahydro-9H-carbazole phenylacetate 6-(butyroyl)amino-3-(diethyl)amino-1,2,3,4-tetrahydro-9H-carbazole bisulfate 6-(pentanoyl)amino-3-(propyl)amino-1,2,3,4-tetrahydro-9H-carbazole hydrochloride 6-(2-methylbutanoyl)amino-3-(1-phenyleth-2-yl)amino-1,2,3,4-tetrahydro-9H-carbazole hydrochloride ...

Patent; Eli Lilly and Company; US5708187; (1998); (A1) English View in Reaxys H N HO O

HN

HN

O

Rx-ID: 25471981 View in Reaxys 293/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

6-(3-furoyl)amino-3-(diethyl)amino-1,2,3,4-tetrahydro-9H-carbazole 6-(2-chloro-4-fluoro)benzoyl-3-(methyl)amino-1,2,3,4-tetrahydro-9H-carbazole 6-(3-pyridinoyl)amino-3-(diethyl)amino-1,2,3,4-tetrahydro-9H-carbazole 6-(3-chloro-2-pyridinoyl)amino-3-(diethyl)amino-1,2,3,4-tetrahydro-9H-carbazole 6-(acetyl)amino-3-(methyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole phenylacetate 6-(butyroyl)amino-3-(butyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole bisulfate 6-(pentanoyl)amino-3-(phenethyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole hydrochloride 6-(2-methylbutanoyl)amino-3-(1-phenyleth-2-yl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole hydrochloride ...

Patent; Eli Lilly and Company; US5708187; (1998); (A1) English View in Reaxys

HO

NH

N

H N

O

O

Rx-ID: 25471998 View in Reaxys 294/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

6-(3-furoyl)amino-3-(diethyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole 6-(2-chloro-4-fluoro)benzoyl-3-(methyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole 6-(3-pyridinoyl)amino-3-(diethyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole 6-(3-chloro-2-pyridinoyl)amino-3-(diethyl)aminomethyl-1,2,3,4-tetrahydro-9H-carbazole 7-(acetyl)amino-4-(phenethyl)aminocyclohepta[7,6-b]indole phenylacetate 7-(butyroyl)amino-4-aminocyclohepta[7,6-b]indole bisulfate 7-(pentanoyl)amino-4-aminocyclohepta[7,6-b]indole hydrochloride 7-(2-methylbutanoyl)amino-4-(1-phenyleth-2-yl)aminocyclohepta[7,6-b]indole hydrochloride

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

89/96

2016-04-10 14:47:02

...

Patent; Eli Lilly and Company; US5708187; (1998); (A1) English View in Reaxys O HN HO

N O

N H

Rx-ID: 25472014 View in Reaxys 295/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

7-(3-furoyl)amino-4-(diethyl)aminocyclohepta[7,6-b]indole 7-(2-chloro-4-fluoro)benzoyl-4-(methyl)aminocyclohepta[7,6-b]indole 7-(3-pyridinoyl)amino-4-(diethyl)aminocyclohepta[7,6-b]indole 7-(3-chloro-2-pyridinoyl)amino-4-(diethyl)aminocyclohepta[7,6-b]indole 7-(acetyl)amino-4-(phenethyl)aminomethylcyclohepta[7,6-b]indole phenylacetate 7-(butyroyl)amino-4-(sec-butyl)aminomethylcyclohepta[7,6-b]indole bisulfate 7-(pentanoyl)amino-4-aminomethylcyclohepta[7,6-b]indole hydrochloride 7-(2-methylbutanoyl)amino-4-(1-phenyleth-2-yl)aminomethylcyclohepta[7,6-b]indole hydrochloride ...

Patent; Eli Lilly and Company; US5708187; (1998); (A1) English View in Reaxys N Cl

HO

O O

N

Cl

OH

HO

HN

Rx-ID: 25486359 View in Reaxys 296/325 Yield

Conditions & References The following group is illustrative of compounds contemplated within the scope of this invention: ...

1-((2S)-hydroxy-3-(2-methyl-4-acetylphenoxy prop-1-yl)-4-hydroxy-4-(quinoxalin-2-yl)piperidine 2-hydroxybenzoate; 1-((2S)-hydroxy-3-(2-benzoyl-4-methylphenoxy)prop-1-yl)-4-hydroxy-4-(isoquinolin-4-yl)piperidine; 1-((2R)-hydroxy-3-(naphth-2-yloxy)prop-1-yl)-4-hydroxy-4-(isoquinolin-4-yl)piperidine; 1-((2R,S)-hydroxy-3-(6-methoxynaph-2-yloxy)prop-1-yl)-4-hydroxy-4-(isoquinolin-4-yl)piperidine phthalate; 1-((2R)-hydroxy-3-(6,7-dichloroindol-4-yloxy)prop-1-yl)-4-hydroxy-4-(isoquinolin-4-yl)piperidine phenylacetate; 1-((2S)-hydroxy-3-(2-isopropylindol-5-yloxy)prop-1-yl)-4-hydroxy-4-(pyridinin-3-yl)piperidine citrate; 1-((2R)-hydroxy-3-(2-methyl-7-chloroindol-5-yloxy)prop-1-yl)-4-hydroxy-4-(quinoxalin-3-yl)piperidine lactate; 1-((2R,S)-hydroxy-3-(1-isopropyl-6-methyl-7-chloro-indol-4-yloxy)prop-1-yl)-4-hydroxy-4-(isoquinolin-4-yl)piperidine glycollate; ...

Patent; Eli Lilly and Company; US6242450; (2001); (B1) English View in Reaxys

O

O

O

OH

Rx-ID: 25506534 View in Reaxys 297/325 Yield

Conditions & References 25 : Compound (20): 2-(4'-acetoxy-2'-methylphenyl)-prop-2-en phenylacetate Compound (20): 2-(4'-acetoxy-2'-methylphenyl)-prop-2-en phenylacetate

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

90/96

2016-04-10 14:47:02

1H-NMR

(500 MHz, CDCl3): δ 7.35 (d, 1H, J=7.5 Hz), 7.05 (d, 1H, J=7.5 Hz), 6.87 (s, 1H), 4.51 (d, 1H, J=12.0 Hz),

4.23 (d, 1H, J=12.0 Hz), 3.02 (d, 1H, J=12.0 Hz), 2.80 (d, 1H, J=12.0 Hz), 2.58 (m, 2H), 2.35 (s, 3H), 2.02 (s, 3H), 1.74 (m, 2H), 1.2 (m, 24H), 0.8 (m, 3H) Patent; Zee, Ok Pyo; US6255517; (2001); (B1) English View in Reaxys

HO

13C

O

Rx-ID: 7182539 View in Reaxys 298/325 Yield

Conditions & References Benzyl-MgCl, 13CO2 Olah,G.A.; Porter,R.D.; Journal of the American Chemical Society; vol. 93; (1971); p. 6877 - 6887 View in Reaxys nach Yur'ev, Practical Work in Organic Chemistry, Vol. 1 Izd. MGU (1957), 76 Petrova et al.; Journal of Organic Chemistry USSR (English Translation); vol. 11; (1975); p. 2158,2159-2163; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 2123 View in Reaxys aus Benzylmagnesiumchlorid, 13-CO2 nach Ref.10: M.Calvin, C.Heidelberger, J.C.Reid, B.M.Tolbert u. P.F.Yankwich,'Isotopic Carbon',Wiley,New York,N.Y.1949, p.180 Olah,G.A.; Porter,R.D.; Journal of the American Chemical Society; vol. 92; (1970); p. 7627 - 7629 View in Reaxys 2H

HO O

Rx-ID: 7390188 View in Reaxys 299/325 Yield

Conditions & References entspr. Nitril, H2SO4 Gal et al.; Acta Pharmaceutica Suecica; vol. 14; (1977); p. 335,340 View in Reaxys Oxidativer Abbau v. <1-Deutero-allyl>-benzol mit Ozon in Ethylacetat Arnold; Smolinsky; Journal of Organic Chemistry; vol. 25; (1960); p. 129,130 View in Reaxys Benzylbromid, MgBr2 Su,D.T.T.; Thornton,E.R.; Journal of the American Chemical Society; vol. 100; nb. 6; (1978); p. 1872 - 1875 View in Reaxys H

14C 2

HO O

Rx-ID: 7655284 View in Reaxys 300/325 Yield

Conditions & References 2-Phenylacrylsaeure, geschmolzenes Alkali <2 - 3 Min.> Δ, neben Ameisensaeure u. gasf. Produkten Bonner; Rewick; Journal of the American Chemical Society; vol. 84; (1962); p. 2334,2336 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

91/96

2016-04-10 14:47:02

F

B

F

HO O

F

Rx-ID: 8220781 View in Reaxys 301/325 Yield

Conditions & References Herstellung von <Pentadeuterio-phenyl>-essigsaeure Moss; Schoenheimer; Journal of Biological Chemistry; vol. 135; (1940); p. 415,417, 423 View in Reaxys H

13C 2

HO O

Rx-ID: 7182469 View in Reaxys 302/325 Yield

Conditions & References Benzylmagnesiumchlorid, Carboxylierung Brown,R.F.C. et al.; Australian Journal of Chemistry; vol. 30; (1977); p. 1757 - 1767 View in Reaxys C6H5-13CH2-MgCl, CO2 Horie; Baba; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 4; (1978); p. 1009 - 1014 View in Reaxys

HO

H

13C

13C 2

O

Rx-ID: 7187131 View in Reaxys 303/325 Yield

Conditions & References (α-13C)-Benzylmagnesiumchlorid, 13CO2 Pomerantz; Fink; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 16; nb. 2; (1979); p. 275 - 286 View in Reaxys C6H5-13CH2-MgCl, 13CO2 Horie; Baba; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 4; (1978); p. 1009 - 1014 View in Reaxys 2H

HO O

Rx-ID: 7390050 View in Reaxys 304/325 Yield

Conditions & References aus C6H5CH2COOH via Thalliumverb. mit C2H5OD u. NaBH4 Herbert; Tetrahedron Letters; (1973); p. 1375 View in Reaxys 2H

O 2H

O2H 2

H

2H 2H

2H 2

H

Rx-ID: 7660222 View in Reaxys 305/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

92/96

2016-04-10 14:47:02

Yield

Conditions & References Aus Benzylcyanid mit NaOD/D2O Hinrichs; Kurreck; Niemeier; Tetrahedron; vol. 30; nb. 2; (1974); p. 315 - 320 View in Reaxys

HO O O

Rx-ID: 8360995 View in Reaxys 306/325 Yield

Conditions & References Komponenten Agranat; Cohen; Bulletin of the Chemical Society of Japan; vol. 47; (1974); p. 723 View in Reaxys

N

HO O

N H

Rx-ID: 8348855 View in Reaxys 307/325 Yield

Conditions & References Komponenten Duff et al.; Journal of Chemical Education; vol. 46; (1969); p. 388; ; vol. 71; nb. 61335a; (1969) View in Reaxys

HO N

O HN

Rx-ID: 8361925 View in Reaxys 308/325 Yield

Conditions & References Komponenten Duff et al.; Journal of Chemical Education; vol. 46; (1969); p. 388; ; vol. 71; nb. 61335a; (1969) View in Reaxys

HO O

2H

Rx-ID: 7181172 View in Reaxys 309/325 Yield

Conditions & References 4-Bromphenylessigsaeure, NaOD Langhals; Fischer; Chemische Berichte; vol. 111; (1978); p. 543,545, 547, 548 View in Reaxys

2H

HO O 2H

Rx-ID: 7184202 View in Reaxys 310/325 Yield

Conditions & References 4-Aminophenylessigsaeure, NaNO2 / H+

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

93/96

2016-04-10 14:47:02

Langhals; Fischer; Chemische Berichte; vol. 111; (1978); p. 543,545, 547, 548 View in Reaxys 3H 3H

HO O

3

H

Rx-ID: 7187338 View in Reaxys 311/325 Yield

Conditions & References Alanin I, Chloramin T Clifford et al.; Journal of Labelled Compounds; vol. 11; (1975); p. 435,436,440,442 View in Reaxys

O O

(v1)

Rx-ID: 7389218 View in Reaxys 312/325 Yield

Conditions & References α-Phenylacetylbromid, γ-Radiolyse Ito et al.; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol.

74; (1978); p. 1188,1192 View in Reaxys 3H

HO O

Rx-ID: 7655052 View in Reaxys 313/325 Yield

Conditions & References Phenylessigsaeure in 30percentig. wss. NaOH u. T-haltiges W. im Rohr (18 h, 100 grad) Simon; Muellhofer; Chemische Berichte; vol. 97; (1964); p. 2202,2207 View in Reaxys

3H

O O

Rx-ID: 7655071 View in Reaxys 314/325 Yield

Conditions & References Satchell; Journal of the Chemical Society; (1961); p. 3822,3825 View in Reaxys

HO O

3H

Rx-ID: 7685776 View in Reaxys 315/325 Yield

Conditions & References p-Bromphenylessigsaeureethylester, 3H2-Gas, Pd/Aktivkohle-Katalysator Gosztonyi; Isacson; Journal of Labelled Compounds; vol. 5; (1969); p. 281 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

94/96

2016-04-10 14:47:02

H C O O–

Rx-ID: 8320906 View in Reaxys 316/325 Yield

Conditions & References Phenylessigsaeure, O-* Neta et al.; Journal of Physical Chemistry; vol. 76; (1972); p. 847 View in Reaxys

2 Cl –

–

O

2 O Zr 4+

Rx-ID: 8333365 View in Reaxys 317/325 Yield

Conditions & References ZrCl4, Phenylessigsaeure, (110grad) Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

–O

3

Cl –

O Zr 4+

Rx-ID: 8343675 View in Reaxys 318/325 Yield

Conditions & References ZrCl4, Phenylessigsaeure,(3Mol), (120grad) Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

O 4

Ti4+

O–

Rx-ID: 8345590 View in Reaxys 319/325 Yield

Conditions & References TiCl4, Phenylessigsaeure (Ueberschuss), Diethylether Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

–

O

4

Zr 4+

O

Rx-ID: 8354898 View in Reaxys 320/325 Yield

Conditions & References ZrCl4, Phenylessigsaeure (Ueberschuss), (135grad) Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

2 Cl –

O 2 O– Ti4+

Rx-ID: 8361548 View in Reaxys 321/325

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

95/96

2016-04-10 14:47:02

Yield

Conditions & References TiCl4, 2Mol Phenylessigsaeure, Diethylether Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

3 Cl –

O O– Ti4+

Rx-ID: 8361549 View in Reaxys 322/325 Yield

Conditions & References TiCl4, 1Mol Phenylessigsaeure, Diethylether Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

O 3

Cl –

O– Ti4+

Rx-ID: 8361551 View in Reaxys 323/325 Yield

Conditions & References TiCl4, 3Mol Phenylessigsaeure, Diethylether Jaura et al.; Journal of the Indian Chemical Society; vol. 39; (1962); p. 531 View in Reaxys

N HO O

Rx-ID: 8369723 View in Reaxys 324/325 Yield

Conditions & References aus den Komponenten Patent; Gallardo; ES350757; (1969); ; vol. 72; nb. 12587w; (1970) View in Reaxys

N

O HO

Rx-ID: 28308138 View in Reaxys 325/325 Yield

Conditions & References 147 Patent; BIONIQS LIMITED; WO2009/34329; (2009); (A1) English View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

96/96

2016-04-10 14:47:02