[CH3:1][N:2]([CH3:14])[C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:4]=1[C:5]#[N:6].Cl>[Fe].CO>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:3]([N:2]([CH3:14])[CH3:1])[C:4]=1[C:5]#[N:6]To a suspension of 5.7 g. of 2-dimethylamino-6-nitrobenzonitrile in 20 ml. of methanol and 17 ml. of concentrated hydrochloric acid is added 5.3 g. of iron powder in portions. The mixture is stirred for 1/2 hour, diluted with 200 ml. of water and extracted with methylene chloride which is dried and evaporated in vacuo to yield crude 2-amino-6-dimethylaminobenzonitrile.
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