[H-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[F:12][C:13]1[CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.Cl>CN(C)C=O.O>[F:12][C:13]1[CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:17][C:18]=1[NH:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7]
21.8 g (0.5 mol) of sodium hydride were added in portions to a solution of 59 g (0.5 mol) of 2-aminobenzonitrile and 53.2 ml (0.5 mol) of 3-fluoronitrobenzene in absolute dimethylformamide, whereby the reaction mixture warmed up to 80° C., with a change in colour from dark green to dark red. After the mixture had been cooled to room temperature, it was diluted with water and acidified with 2N hydrochloric acid, and the precipitate formed was filtered off. The precipitate was purified by chromatography over silica gel using dichloromethane, and the residue from evaporation of the product-containing fractions was thoroughly stirred with ether/petroleum ether 1:2.
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