4-Nitrobenzaldehyde → N-(4-nitrobenzylidene)-N'-(4-trifluoromethoxyphenyl)-hydrazine

Participants

Reaction Steps

To a magnetically stirred solution of 4-nitrobenzaldehyde (1.57 g, 10.41 mmoL) dissolved in EtOH (21 mL) was added (4-(trifluoromethoxy)phenyl)-hydrazine (2 g, 10.41 mmoL) and the reaction was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and dried under high vacuum to give the title compound as a mixture of E and Z-isomers (3.35 g, 99%): 1H NMR (400 MHz, CDCl3) δ 10.17 (s, 1H), 8.40 (d, J=8.6 Hz, 2H, isomer A), 8.24 (d, J=8.6 Hz, 2H, isomer B), 8.08 (d, J=8.7 Hz, 2H, isomer A), 7.79-7.74 (m, 4H, mixture of isomers A & B), 7.19-7.13 (m, 6H, mixture of isomers A & B); 19F NMR (376 MHz, CDCl3) δ −58.34; ESIMS m/z 325 ([M+H])+.

Provenance & Evidence