Benzylamine → 2-(Benzylamino)nicotinic acid

Participants

Reaction Steps

Benzylamine (14 mL, 126.8 mmol) was added to a solution of chloronicotinic acid (10 g, 63.4 mmol) in pyridine and refluxed overnight. The pyridine was distilled and the residue was dissolved in 1N NaOH. The solution was diluted with water to adjust the pH to 10 to 11 and washed by dichloromethane. The aqueous phase was neutralized with cold aqueous 10% HCl solution to adjust the pH to 6 to 7. The solids formed were filtered, washed with cold water, and dried in a vacuum oven to yield 12.2 g (84%) of 2-benzylamino nicotinic acid (1) as white solids. MP: 148° C.; 1H-NMR (DMSO-d6): δ 4.69 (d, J=3.6 Hz, 2H), 6.61 (dd, J=4.9, 7.7 Hz, 1H), 7.23 (m, 1H), 7.29 (m, 4H), 8.08 (dd, J=1.8, 7.0 Hz, 1H), 8.28 (dd, J=1.8, 7.0 Hz, 1H), 8.47 (br. s, 1H), 13.10 (s, 1H); EIMS: 229 (M+1), 251 (M+23).

Provenance & Evidence