2-(2,5-Dimethoxyphenyl)acetonitrile [C10H11NO2]

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Date

18 reactions in Reaxys

2018-04-07 07h:21m:11s (UTC)

O

1. Query

O

N

Search as: As drawn

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O

O

O

HO

O O

N

Rx-ID: 25932751 View in Reaxys 1/18 Yield

Conditions & References

80 %

With sodium azide, TEA, triethylphosphine, (bis-(2-methoxyethyl)amino)sulfur trufluoride 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 -1

F

O

(v4)

F

B FF

O O

N O

N+

O

O

N

N

O

O

O

O

O

N

O

O O

N

O

O

N

N

N

O

O

Rx-ID: 4839290 View in Reaxys 2/18 Yield

Conditions & References in acetonitrile, Time= 8h Kosynkin, Dmitry; Bockman, T. Michael; Kochi, Jay K.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1997); p. 2003 - 2012 View in Reaxys

Cl

O

N

O

F

N+

O

-1 Cl

F F

F (v6)

Cl

F

F

Cl

F

O

F

Cl

P F

F Cl

Cl

F

O O

Cl

Cl

F

N

Rx-ID: 4839291 View in Reaxys 3/18 Yield

Conditions & References

32 %

in acetonitrile, Time= 8h Kosynkin, Dmitry; Bockman, T. Michael; Kochi, Jay K.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1997); p. 2003 - 2012 View in Reaxys

O

F

F

O N

O

F

O

N2

O O

F

F

N

Rx-ID: 7455824 View in Reaxys 4/18 Yield

Conditions & References Time= 8h Kosynkin, Dmitry; Bockman, T. Michael; Kochi, Jay K.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1997); p. 2003 - 2012 View in Reaxys

Copyright © 2018 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.

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O

O

O

O

Z N

HO

O N

HO

Rx-ID: 3072325 View in Reaxys 5/18 Yield

Conditions & References

88 %

With 1,1'-carbonyldiimidazole in benzene, 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h Kitagawa; Kawaguchi; Inoue; Katayama; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 11; (1991); p. 3030 - 3033 View in Reaxys

O

O O

O

HO

S

O

N

Rx-ID: 20345628 View in Reaxys 6/18 Yield

Conditions & References Reaction Steps: 2 1: 96 percent / hydroxylamine / ethanol / 1 h / Ambient temperature 2: 88 percent / 1,1'-carbonyldiimidazole / benzene / 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h With hydroxylamine, 1,1'-carbonyldiimidazole in ethanol, benzene Kitagawa; Kawaguchi; Inoue; Katayama; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 11; (1991); p. 3030 - 3033 View in Reaxys N O

O

Br

O O

O

N

O O O

N

Rx-ID: 3738180 View in Reaxys 7/18 Yield

Conditions & References

81 %, 12 %

With ethoxyethoxyethanol, sodium amide in 1,2-dimethoxyethane, 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 2 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

Br O

O

N

O

N

Rx-ID: 3738179 View in Reaxys 8/18 Yield

Conditions & References With potassium amide, 1.) liq. NH3, 2.) 1 h, Yield given. Multistep reaction Han, Yu Xin; Jovanovic, Misa V.; Biehl, Edward R.; Journal of Organic Chemistry; vol. 50; nb. 8; (1985); p. 1334 - 1337 View in Reaxys

Copyright © 2018 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.

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O N Cl

O

O

O

N

Rx-ID: 2893559 View in Reaxys 9/18 Yield

Conditions & References

16.3 %

in acetonitrile, Irradiation, Mechanism Kurz, M. E.; Lapin, S. C.; Miriam, K.; Hagen, T. J.; Qian, X. Q.; Journal of Organic Chemistry; vol. 49; (1984); p. 2728 2733 View in Reaxys

16.3 %

in acetonitrile, Irradiation Kurz, M. E.; Lapin, S. C.; Miriam, K.; Hagen, T. J.; Qian, X. Q.; Journal of Organic Chemistry; vol. 49; (1984); p. 2728 2733 View in Reaxys

16.3 %

in acetonitrile, Time= 22h, Irradiation Lapin, Stephen; Kurz, Michael E.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1981); p. 817 - 818 View in Reaxys

O O

O N

Na

O

Cl

N

Rx-ID: 2117510 View in Reaxys 10/18 Yield

Conditions & References With sodium iodide in dimethyl sulfoxide, Time= 16h, T= 90 °C , Yield given Parker; Kallmerten; Journal of Organic Chemistry; vol. 45; nb. 13; (1980); p. 2614 - 2620 View in Reaxys

O O

O

O OH

N

Rx-ID: 21200355 View in Reaxys 11/18 Yield

Conditions & References Reaction Steps: 2 1: HCl / benzene 2: NaI / dimethylsulfoxide / 16 h / 90 °C With hydrogenchloride, sodium iodide in dimethyl sulfoxide, benzene Parker; Kallmerten; Journal of Organic Chemistry; vol. 45; nb. 13; (1980); p. 2614 - 2620 View in Reaxys Reaction Steps: 2 1: pyridine; SOCl2 With pyridine, thionyl chloride Harley-Mason; Jackson; Journal of the Chemical Society; (1954); p. 1165,1168 View in Reaxys

Copyright © 2018 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.

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O O

O

O O

N

Rx-ID: 21229680 View in Reaxys 12/18 Yield

Conditions & References Reaction Steps: 3 1: NaBH4 / ethanol / 0 °C 2: HCl / benzene 3: NaI / dimethylsulfoxide / 16 h / 90 °C With hydrogenchloride, sodium tetrahydroborate, sodium iodide in ethanol, dimethyl sulfoxide, benzene Parker; Kallmerten; Journal of Organic Chemistry; vol. 45; nb. 13; (1980); p. 2614 - 2620 View in Reaxys Reaction Steps: 3 1: platinum; ethanol / Hydrogenation 2: pyridine; SOCl2 With pyridine, thionyl chloride, ethanol, platinum Harley-Mason; Jackson; Journal of the Chemical Society; (1954); p. 1165,1168 View in Reaxys

O

O

N

Rx-ID: 7190558 View in Reaxys 13/18 Yield

Conditions & References Moore; Capaldi; Journal of Organic Chemistry; vol. 29; (1964); p. 2860 View in Reaxys Kalra et al.; Indian Journal of Chemistry; vol. 5; (1967); p. 287,289 View in Reaxys Farkas; Varady; Acta Chimica Academiae Scientiarum Hungaricae; vol. 38; (1963); p. 283,285 View in Reaxys Dirania; Chemistry and Industry (London, United Kingdom); (1977); p. 278 View in Reaxys Farkas; Varady; Magyar Kemiai Folyoirat; vol. 69; nb. 10; (1963); p. 458,459-460; ; vol. 60; nb. 7980c; (1964) View in Reaxys

O O

O

O Br

N

Rx-ID: 290781 View in Reaxys 14/18 Yield

Conditions & References Green et al.; Journal of the Chemical Society; (1959); p. 3362,3369 View in Reaxys

O N

K

O

N

Rx-ID: 595832 View in Reaxys 15/18

Copyright © 2018 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.

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Yield

Conditions & References With ethanol Harley-Mason; Jackson; Journal of the Chemical Society; (1954); p. 1165,1168 View in Reaxys With 1,4-dioxane Green et al.; Journal of the Chemical Society; (1959); p. 3362,3369 View in Reaxys

O

O

O

O

N

Rx-ID: 22334132 View in Reaxys 16/18 Yield

Conditions & References Reaction Steps: 2 1: dibenzoyl peroxide; CCl4; N-bromo-succinimide With tetrachloromethane, N-Bromosuccinimide, dibenzoyl peroxide Green et al.; Journal of the Chemical Society; (1959); p. 3362,3369 View in Reaxys

O O

O

O Cl

N

Rx-ID: 341851 View in Reaxys 17/18 Yield

Conditions & References Harley-Mason; Jackson; Journal of the Chemical Society; (1954); p. 1165,1168 View in Reaxys

O

O O HO

O

O

O

N

Rx-ID: 483145 View in Reaxys 18/18 Yield

Conditions & References With acetic anhydride Sugasawa; Shigehara; Chemische Berichte; vol. 74; (1941); p. 459,462 View in Reaxys

Copyright © 2018 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.

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