Benzaldehyde → 6-(2-Benzylidenehydrazinyl)-3-chloro-4-(pyrrolidin-1-yl)pyridazine

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Reaction Conditions

Reaction Steps

To a solution of 6-chloro-5-(pyrrolidin-1-yl)pyridazin-3-ylhydrazine (14 g, 0.063 mol) in 0.1 N hydrochloric acid (600 ml) was added benzaldehyde (6.4 ml, 0.063 mol) dropwise at room temperature. The mixture was stirred at 60° C. for 15 min, yielding a thick slurry. The pH of the solvent was adjusted to ˜11 with 4 N aqueous sodium hydroxide solution, and the precipitate filtered off. The residue was washed with water, ethanol and diethyl ether, yielding the title compound as a white solid (14 g, 73%). 1H NMR (360 MHz, DMSO) δ1.93 (4H, m), 3.58 (4H, m), 6.57 (1H, s), 7.35 (1H, m), 7.39 (2H, m), 7.66 (2H, d, J=7.1 Hz), 8.06 (1H, s), 11.16 (1H, s). MS (ES+) m/e 302 [MH]+, 304 [MH]+.

Provenance & Evidence