Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 178492066, compound

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Reaction Steps

Following a similar procedure to that described in Example 4, except using ethyl 4-chloro-2-methyl-3-phenyl-5-pyridinecarboxylate and 4-methoxyphenylhydrazine hydrochloride instead of ethyl 4-chloro-3-propyl-5-pyridinecarboxylate and 4-chlorophenylhydrazine hydrochloride, the title compound was prepared, after further purification by flash chromatography (silica gel, 5% MeOH/CH2Cl2) and recrystallization (CH2Cl2-MeOH-EtOAc), in 4% yield as a yellow solid; mp 300-310° C.; 1H NMR (360 MHz, DMSO-d6) δ2.25 (3H, s), 3.74 (3H, s), 6.93 (2H, d, J 9.2 Hz), 7.43 (1H, m), 7.47-7.51 (4H, m), 7.95 (21H, d, J 9.1 Hz), 8.50(1H, s), 12.34 (1H, br s); MS (ES+) m/z 332 [MH]+. Anal. found: C, 72.15; H, 4.84; N, 12.66. C20H17ClN3O2 requires: C, 72.49; H, 5.17; N, 12.68%.

Provenance & Evidence