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A mixture of 4-amino-benzonitrile (11.8 g, 100 mmol) and 3-nitro-benzaldehyde (16.6 g, 110 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 3 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(3-nitro-benzylidene)-amino]-benzonitrile (21 g, 83%) as a white solid: LC/MS m/e calcd for C14H9N3O2 (M+H)+: 252.25, observed: 252.1.

1. customwas prepared
2. temperatureThe reaction mixture was heated
3. temperatureto reflux for 3 h
4. customThe solvent was removed in vacuo
5. washthe residue was washed with ether