Dimethylformamide → 2-(2-Methoxyphenyl)-2-methylpropanenitrile

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][C:6]#N.[CH3:12]I.[H-].[Na+].C[N:17]([CH3:20])C=O>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([C:20]#[N:17])([CH3:12])[CH3:6]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 81496(2-Methoxyphenyl)acetonitrile

Product 1

HCID 101979202-(2-Methoxyphenyl)-2-methylpropanenitrileYield 85%

Procedure

By a method analogous to that of Example 3(a), o-methoxybenzyl cyanide was methylated with methyl iodide and sodium hydride in dimethylformamide to give the desired compound in 85% yield.

Sources & evidence

ORD record: ord-54a92743cfab4463b065fcea4c820525
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04263037

Reaction notes

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