Phenylhydrazine → 4-(Diphenylamino) benzaldehyde phenylhydrazone

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A mixture of 4-(diphenylamino)benzaldehyde (10 g, 0.037 mol) and 300 ml of methanol was added to 500 ml 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The mixture was mildly heated by a heating mantle until all solid entered into solution. Then a solution of N-phenylhydrazine (5.94 g, 0.055 mol, from Aldrich, Milwauke, Wis.) in 50 ml of methanol was added. The reaction mixture was refluxed for 0.5 hour and then cooled to room temperature. The yellow precipitated product was filtered off, washed with a large amount of methanol, and dried to yield 11.7 g (86.7%) of 4-(diphenylamino)benzaldehyde N-phenylhydrazone. The melting point was found to be 168–169° C. The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 6.55–7.64 (m, 21H, Ar, ═CH, —NH). The IR spectrum of the product was characterized by the following absorption frequencies (KBr, cm−1): ν(N—H) 3294, ν(arene C—H) 3026, ν(C═C in Ar) 1595; 1489, ν(C—N) 1282; 1257, γ(Ar) 750; 731. The mass spectrum of the product was characterized by the following mass peaks (m/z): 364 (100%, M+1), 314, 223, 159.

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