4-Fluorophenylhydrazine hydrochloride → HCID 178433650, compound

Participants

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-fluorophenylhydrazine 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), in 19% yield as a yellow solid; mp 303-317° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ2.25 (3H, s), 7.20 (2H, t, J 9.0 Hz), 7.42 (1H, m), 7.50-7.51 (4H, m), 8.09 (2H, dd, J 9.2, J′5.2 Hz), 8.55 (1H, d), 12.43 (1H, br s); MS (ES+) m/z 320 [MH]+. Anal. found: C, 69.91; H, 4.15; N, 13.25. C19H14FN3Oe.0.3H2O requires: C, 70.27; H, 4.53; N, 12.94%.

Provenance & Evidence