Benzylamine → N-benzyl-2-chloropyridine-4-carboxamide

Participants

Reaction Steps

A solution of 2-chloroisonicotinic acid (5.00 g, 31.7 mmol) in thionyl chloride (25 mL) was refluxed for 30 minutes and concentrated in vacuo to dryness. The residue was dissolved in dichloromethane (100 mL) and added to a mixture of benzylamine (3.40 g, 31.7 mmol) and triethylamine (6.64 mL, 47.6 mmol) in dichloromethane (40 mL). The resulting solution was stirred at ambient temperature for 16 hours, washed with saturated sodium bicarbonate solution (30 mL), water (30 mL) and brine (30 mL). The separated organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with 60-80% ethyl acetate in hexanes to give N-benzyl-2-chloroisonicotinamide as a colorless solid (5.35 g, 49%): 1H NMR (300 MHz, DMSO-d6) δ 9.44-9.40 (m, 1H), 8.56 (d, J=5.1 Hz, 1H), 7.91 (s, 1H), 7.82-7.80 (m, 1H), 7.34-7.25 (m, 5H), 4.49 (d, J=5.1 Hz, 2H), MS (ES+) m/z 247.2 (M+1).

Provenance & Evidence