2-(3,4,5-trimethoxyphenyl)acetonitrile [CAS 13338-63-1; InChIKey ACFJNTXCEQCDBX-UHFFFAOYSA-N;

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27 reactions in Reaxys

2016-03-15 15h:21m:48s (EST)

N

O

1. Query O O

Search as: As drawn

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O O

OH

O O

N

O

O O

Rx-ID: 25932753 View in Reaxys 1/27 Yield

Conditions & References

88 %

With sodium azide, TEA, diethylphosphinoethane, [bis(2-methoxyethyl)amino]-sulfur trifluoride in dichloromethane, dimethyl sulfoxide, Time= 50h, T= 0 °C Kangani, Cyrous O.; Day, Billy W.; Kelley, David E.; Tetrahedron Letters; vol. 49; nb. 5; (2008); p. 914 - 918 View in Reaxys

O

O

O O

O O

Z N

N O

OH

OH

Rx-ID: 503720 View in Reaxys 2/27 Yield

Conditions & References

88 %

With oxalic acid diimidazolide in benzene, 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h Kitagawa; Kawaguchi; Ikiuchi; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 1; (1991); p. 187 - 189 View in Reaxys With acetic anhydride Baker; Robinson; Journal of the Chemical Society; (1929); p. 147 View in Reaxys With acetic anhydride, Time= 0.0833333h, Heating Shaw; Srivastava; Jha; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 144 - 147 View in Reaxys

O

O

O O

N OH

O

O

Rx-ID: 15091421 View in Reaxys 3/27 Yield

Conditions & References Reaction Steps: 2 1: SOCl2 / dioxane / 20 °C 2: acetonitrile / 20 °C With thionyl chloride in 1,4-dioxane, acetonitrile Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 16; (2001); p. 2205 - 2208 View in Reaxys Reaction Steps: 2 1: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp.

2: 75 percent / dimethylsulfoxide / Ambient temperature With phosphorus tribromide, triethylamine in tetrachloromethane, dimethyl sulfoxide Patra, Amarendra; Mukhopadhyay, Prabir K.; Ghosh, Gargi; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 3; (1982); p. 173 - 175 View in Reaxys

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Reaction Steps: 5 1: pyridinium chlorochromate / CH2Cl2 / 3 h 2: sodium acetate / acetic anhydride / Heating 3: NaOH / H2O / Heating 4: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 5: acetic anhydride / 0.08 h / Heating With sodium hydroxide, hydroxylamine hydrochloride, sodium acetate, acetic anhydride, pyridinium chlorochromate in sodium hydroxide, dichloromethane, water, acetic anhydride Shaw; Srivastava; Jha; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 144 - 147 View in Reaxys Reaction Steps: 2 1: SOCl2, Me2NPh 2: NaI With thionyl chloride, N,N-dimethyl-aniline, sodium iodide Cason,J.; Lynch,D.M.; Journal of Organic Chemistry; vol. 31; (1966); p. 1883 - 1887 View in Reaxys Reaction Steps: 2 1: HCl / benzene / 0 °C 2: dioxane; H2O / Heating With hydrogenchloride in 1,4-dioxane, water, benzene Schwachhofer,G.; Chopin,J.; Bulletin de la Societe Chimique de France; (1962); p. 835 - 843 View in Reaxys Reaction Steps: 2 1: thionyl chloride / dichloromethane 2: dimethyl sulfoxide With thionyl chloride in dichloromethane, dimethyl sulfoxide Zheng, Cheng; Guo, Yibing; Meng, Ying; Dou, Sufeng; Shao, Jian; Yang, Yumin; Indian Journal of Chemistry Section B Organic and Medicinal Chemistry; vol. 52; nb. 5; (2013); p. 654 - 664 View in Reaxys

O

O

O O

N Cl

O

O

Rx-ID: 24968902 View in Reaxys 4/27 Yield

Conditions & References W.16.1 : (1) (1) Synthesis of (3,4,5-trimethoxy)phenylacetonitrile STR133 3,4,5-trimethoxy benzyl chloride 7.0 g and sodium cyanide 6.3 g were dissolved into 50 ml of N,N-dimethylformamide and they were then stirred at 80° C. for 45 minutes.

The temperature of the reactive liquid was then lowered down to the room temperature, 200 ml of water was added thereto and then extraction was made thrice by means of 100 of ethyl acetate.

The liquids thus extracted was washed by saturated saline solution, then the solvent was distilled under reduced pressure to have 5.5 g of captioned compound. in water, ethyl acetate, N,N-dimethyl-formamide Patent; Eisai Co., Ltd.; US5037827; (1991); (A1) English View in Reaxys

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O O N

<3,4,5-trimethoxy-benzyl chloride

K

N O

Rx-ID: 7368931 View in Reaxys 5/27 Yield

Conditions & References With methanol Tsao; Journal of the American Chemical Society; vol. 73; (1951); p. 5495 View in Reaxys With methanol Dornow; Petsch; Archiv der Pharmazie (Weinheim, Germany); vol. 285; (1952); p. 323,326 View in Reaxys With ethanol Schiemenz; Engelhard; Chemische Berichte; vol. 92; (1959); p. 1336,1342 View in Reaxys N

O Br

O

O O

O

N

O

N O

O

O

O O

O

Rx-ID: 3738062 View in Reaxys 6/27 Yield

Conditions & References

11 %, 83 % With diethylene glycol monoethyl ether, sodium amide in ethylene glycol dimethyl ether, 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 4.5 h Carre, M. C.; Ezzinadi, A. S.; Zouaoui, M. A.; Geoffroy, P.; Caubere, P.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3323 - 3330 View in Reaxys 83 %, 11 % With diethylene glycol monoethyl ether, sodium amide in ethylene glycol dimethyl ether, 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 4.5 h Carre, M. C.; Ezzinadi, A. S.; Zouaoui, M. A.; Geoffroy, P.; Caubere, P.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3323 - 3330 View in Reaxys

O

O O

O

O

N O

O

O

Rx-ID: 21161512 View in Reaxys 7/27 Yield

Conditions & References Reaction Steps: 3 1: 70 percent / LAH / tetrahydrofuran 2: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp.

3: 75 percent / dimethylsulfoxide / Ambient temperature With lithium aluminium tetrahydride, phosphorus tribromide, triethylamine in tetrahydrofuran, tetrachloromethane, dimethyl sulfoxide Patra, Amarendra; Mukhopadhyay, Prabir K.; Ghosh, Gargi; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 3; (1982); p. 173 - 175 View in Reaxys

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Reaction Steps: 6 1: lithium aluminium hydride / diethyl ether / 3 h / Heating 2: pyridinium chlorochromate / CH2Cl2 / 3 h 3: sodium acetate / acetic anhydride / Heating 4: NaOH / H2O / Heating 5: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 6: acetic anhydride / 0.08 h / Heating With sodium hydroxide, lithium aluminium tetrahydride, hydroxylamine hydrochloride, sodium acetate, acetic anhydride, pyridinium chlorochromate in sodium hydroxide, diethyl ether, dichloromethane, water, acetic anhydride Shaw; Srivastava; Jha; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 144 - 147 View in Reaxys Reaction Steps: 3 1: LiAlH4 / diethyl ether 2: HCl / benzene / 0 °C 3: dioxane; H2O / Heating With hydrogenchloride, lithium aluminium tetrahydride in 1,4-dioxane, diethyl ether, water, benzene Schwachhofer,G.; Chopin,J.; Bulletin de la Societe Chimique de France; (1962); p. 835 - 843 View in Reaxys Reaction Steps: 3 1: lithium aluminium tetrahydride / tetrahydrofuran 2: thionyl chloride / dichloromethane 3: dimethyl sulfoxide With lithium aluminium tetrahydride, thionyl chloride in tetrahydrofuran, dichloromethane, dimethyl sulfoxide Zheng, Cheng; Guo, Yibing; Meng, Ying; Dou, Sufeng; Shao, Jian; Yang, Yumin; Indian Journal of Chemistry Section B Organic and Medicinal Chemistry; vol. 52; nb. 5; (2013); p. 654 - 664 View in Reaxys

O

O

O O

N O

O

O

Rx-ID: 15095253 View in Reaxys 8/27 Yield

Conditions & References Reaction Steps: 3 1: NaBH4 / methanol / 20 °C 2: SOCl2 / dioxane / 20 °C 3: acetonitrile / 20 °C With sodium tetrahydroborate, thionyl chloride in 1,4-dioxane, methanol, acetonitrile Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 16; (2001); p. 2205 - 2208 View in Reaxys Reaction Steps: 4 1: sodium acetate / acetic anhydride / Heating 2: NaOH / H2O / Heating 3: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 4: acetic anhydride / 0.08 h / Heating With sodium hydroxide, hydroxylamine hydrochloride, sodium acetate, acetic anhydride in sodium hydroxide, water, acetic anhydride Shaw; Srivastava; Jha; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 144 - 147 View in Reaxys

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O

O

O O

N

Na

N

Br

O

O

Rx-ID: 2119186 View in Reaxys 9/27 Yield

Conditions & References

75 %

in dimethyl sulfoxide, Ambient temperature Patra, Amarendra; Mukhopadhyay, Prabir K.; Ghosh, Gargi; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 3; (1982); p. 173 - 175 View in Reaxys

O O O

N

O

O

OH

Rx-ID: 22640967 View in Reaxys 10/27 Yield

Conditions & References Reaction Steps: 3 1: H2O 2: dimethylformamide 3: K2CO3 / acetone With potassium carbonate in water, N,N-dimethyl-formamide, acetone Short,J.H. et al.; Tetrahedron; vol. 29; (1973); p. 1931 - 1939 View in Reaxys

O O

O

N

N HO

O O

Rx-ID: 22652672 View in Reaxys 11/27 Yield

Conditions & References Reaction Steps: 2 1: dimethylformamide 2: K2CO3 / acetone With potassium carbonate in N,N-dimethyl-formamide, acetone Short,J.H. et al.; Tetrahedron; vol. 29; (1973); p. 1931 - 1939 View in Reaxys

O O N

O

O

S O

HO

O

N

O

O O

Rx-ID: 4323084 View in Reaxys 12/27 Yield

Conditions & References With potassium carbonate in acetone Short,J.H. et al.; Tetrahedron; vol. 29; (1973); p. 1931 - 1939 View in Reaxys

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O

O

N

O

C–

O

N+

N Cl

O

O

Rx-ID: 8986990 View in Reaxys 13/27 Yield

Conditions & References in acetonitrile, T= 20 °C Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 16; (2001); p. 2205 - 2208 View in Reaxys

O

O

O O

O

N O

O

O

OH

Rx-ID: 21864932 View in Reaxys 14/27 Yield

Conditions & References Reaction Steps: 2 1: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 2: acetic anhydride / 0.08 h / Heating With hydroxylamine hydrochloride, acetic anhydride in sodium hydroxide Shaw; Srivastava; Jha; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 144 - 147 View in Reaxys

O

O

O O

O

N

N

O O O

Rx-ID: 21865468 View in Reaxys 15/27 Yield

Conditions & References Reaction Steps: 3 1: NaOH / H2O / Heating 2: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 3: acetic anhydride / 0.08 h / Heating With sodium hydroxide, hydroxylamine hydrochloride, acetic anhydride in sodium hydroxide, water Shaw; Srivastava; Jha; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 144 - 147 View in Reaxys

O

O

N

C–

Na +

O O

N Cl

O

O

Rx-ID: 29079015 View in Reaxys 16/27 Yield

Conditions & References in acetonitrile, Reflux Shen, Li; Yang, Xiaochun; Yang, Bo; He, Qiaojun; Hu, Yongzhou; European Journal of Medicinal Chemistry; vol.

45; nb. 1; (2010); p. 11 - 18

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View in Reaxys in acetonitrile, Time= 4h, Reflux Liu, Tao; Dong, Xiaowu; Xue, Na; Wu, Rui; He, Qiaojun; Yang, Bo; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 17; nb. 17; (2009); p. 6279 - 6285 View in Reaxys in dimethyl sulfoxide Zheng, Cheng; Guo, Yibing; Meng, Ying; Dou, Sufeng; Shao, Jian; Yang, Yumin; Indian Journal of Chemistry Section B Organic and Medicinal Chemistry; vol. 52; nb. 5; (2013); p. 654 - 664 View in Reaxys

O Br

O

O O

N

N O

O

Rx-ID: 3738061 View in Reaxys 17/27 Yield

Conditions & References With sodium amide, 1.) liquid ammonia, 5 min, 2.) liquid ammonia, 15 min, Yield given. Multistep reaction Razzuk, Aziz; Biehl, Edward R.; Journal of Organic Chemistry; vol. 52; nb. 12; (1987); p. 2619 - 2622 View in Reaxys

O

O

O N

O

Na

N Cl

O

O

Rx-ID: 4332509 View in Reaxys 18/27 Yield

Conditions & References With sodium iodide Cason,J.; Lynch,D.M.; Journal of Organic Chemistry; vol. 31; (1966); p. 1883 - 1887 View in Reaxys

O

O O

O

O

N O O

N

Rx-ID: 385297 View in Reaxys 19/27 Yield

Conditions & References With sodium sulfate, ethanethiol, zinc(II) chloride, weiteres Reagens: Benzol; Erwaermen des Reaktionsprodukts mit Raney-Nickel in wss. Methanol Schiemenz; Engelhard; Chemische Berichte; vol. 92; (1959); p. 1336,1342 View in Reaxys

O O

EN

OH

O N

O

O O

Rx-ID: 483923 View in Reaxys 20/27 Yield

Conditions & References With acetic anhydride

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Hahn; Wassmuth; Chemische Berichte; vol. 67; (1934); p. 696,702 View in Reaxys

O

O

O N

K

O

N O

O

O

Rx-ID: 590469 View in Reaxys 21/27 Yield

Conditions & References With water, chloroformic acid ethyl ester, magnesium sulfate, Hydrieren des Reaktionsprodukts an Palladium in Benzol Kindler; Schrader; Archiv der Pharmazie (Weinheim, Germany); vol. 283; (1950); p. 190 View in Reaxys

O

O O

O

O

N Cl

O

O

Rx-ID: 22021280 View in Reaxys 22/27 Yield

Conditions & References Reaction Steps: 2 2: ethanethiol; ZnCl2; Na2SO4 / weiteres Reagens: Benzol; Erwaermen des Reaktionsprodukts mit Raney-Nickel in wss. Methanol With sodium sulfate, ethanethiol, zinc(II) chloride Schiemenz; Engelhard; Chemische Berichte; vol. 92; (1959); p. 1336,1342 View in Reaxys

O

O

O O

N O O

Rx-ID: 22080884 View in Reaxys 23/27 Yield

Conditions & References Reaction Steps: 3 1: ozone; ethyl acetate; oxygen / -15 °C / und anschliessende Hydrierung an Palladium/Calciumcarbonat unter Kuehlung; Isolierung als Natriumhydrogensulfit-Addukt 3: acetic acid anhydride With oxygen, acetic anhydride, ozone, ethyl acetate Hahn; Wassmuth; Chemische Berichte; vol. 67; (1934); p. 696,702 View in Reaxys

O

O O

O

O

N O O

Rx-ID: 22082416 View in Reaxys 24/27 Yield

Conditions & References Reaction Steps: 2 2: acetic acid anhydride With acetic anhydride

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Hahn; Wassmuth; Chemische Berichte; vol. 67; (1934); p. 696,702 View in Reaxys

O

O

O N

O

K

N Cl

O

O

Rx-ID: 4144165 View in Reaxys 25/27 Yield

Conditions & References in 1,4-dioxane, water, Heating Schwachhofer,G.; Chopin,J.; Bulletin de la Societe Chimique de France; (1962); p. 835 - 843 View in Reaxys

O

O O

O

O

O

O

O Z N

O

N O

OH

OH

Rx-ID: 568342 View in Reaxys 26/27 Yield

Conditions & References Baker; Robinson; Journal of the Chemical Society; (1929); p. 159; Journal of the Chemical Society; (1926); p. 2718 View in Reaxys

O O N O

Rx-ID: 7368930 View in Reaxys 27/27 Yield

Conditions & References Farkas; Varady; Acta Chimica Academiae Scientiarum Hungaricae; vol. 32; (1962); p. 103,104 View in Reaxys Telang; Smith; Journal of pharmaceutical sciences; vol. 59; nb. 10; (1970); p. 1521 - 1523 View in Reaxys Steck et al.; Journal of Organic Chemistry; vol. 28; (1963); p. 2233,2234 View in Reaxys Farkas et al.; Chemische Berichte; vol. 96; (1963); p. 1865,1866 View in Reaxys Kametani et al.; Yakugaku Zasshi; vol. 86; (1966); p. 913,917; ; vol. 65; nb. 28631; (1966) View in Reaxys Nabil Aboul-Enein; Eid; Acta Pharmaceutica Suecica; vol. 16; nb. 4 suppl; (1979); p. 267 - 270 View in Reaxys Abdel-Rahman et al.; Journal of Chemistry of the United Arab Republic; vol. 11; (1968); p. 401 View in Reaxys Cooke; Rainbow; Australian Journal of Chemistry; vol. 27; (1974); p. 2291 View in Reaxys Kametani et al.; Chemical and Pharmaceutical Bulletin; vol. 16; (1968); p. 1584,1587 View in Reaxys

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