Aniline → HCID 22406920, compound

Participants

Reaction Steps

6-Chloro-3-pyridinecarboxylic acid (15.76 g, 0.1 mole) and aniline (9.3 g, 0.1 mole) were heated together in 50 mL xylene at 180°-185° C. (oil bath) for 3 hours. After cooling, the solid that formed was filtered and washed with Et2O. The solid was triturated with NaHCO3 solution (pH 8), then filtered to give 7.0 g (24%) of N-phenyl-6-(phenylamino)-3-pyridinecarboxamide. The aqueous NaHCO3 solution was carefully neutralized with glacial HOAc (pH 6), and the solid that precipitated was filtered and washed (H2O and with Et2O); yield 12.13 g (57%), mp 264°-266° C. MS (EI) m/e 214 (M+), 213 (M-1, base), 169 (M-45), 167 (M-47).

Provenance & Evidence