Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 178439621, compound

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Reaction Steps

A mixture of ethyl 4-chloro-3-propyl-5-pyridinecarboxylate (0.3199 g, 1.40 mmol) and 4-chlorophenylhydrazine hydrochloride (0.3019 g, 1.69 mmol) in anhydrous 1-butanol (12 ml) was degassed by evaporating the flask under vacuum and refilling with nitrogen several times and then stirred at reflux under nitrogen for 4 h. After leaving to cool overnight, the mixture was filtered, and the solid was washed with ethyl acetate and dried at 60° C. under vacuum to afford 0.2454 g (54%) of the title compound as a yellow solid; mp 213-218° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ0.94 (3H, t, J 7.4 Hz), 1.76 (2H, m), 2.64 (2H, t, J 7.3 Hz), 7.41 (1H, s), 7.48 (2H, d, J 9.0 Hz), 8.24 (2H, d, J 8.9 Hz), 8.52 (1H, s), 12.36 (1H, br s); MS (ES+) m/z 288/290 [MH]+. Anal. found: C, 56.13; H, 4.64; N, 13.02. C15H14CIN3O.0.9HCl requires: C, 56.20; H, 4.69; N, 13.11%.

Provenance & Evidence