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A mixture of 4-chloro-phenylamine (6.4 g, 50 mmol) and 3-nitro-benzaldehyde (8.31 g, 55 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-chloro-phenyl)-(3-nitro-benzylidene)-amine (12 g, 92%) as a light yellow oil: LC/MS m/e calcd for C13H9ClN2O2 (M+H)+: 261.68, observed: 261.0.

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