Triethylamine → 6-Chloro-N-methoxy-N-methylnicotinamide

Participants

Reaction Steps

Oxalyl chloride 12.1 g (95.2 mmol) was added dropwise to a solution of 6-chloronicotinic acid 10.0 g (63.5 mmol) in 100 mL tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h, and then concentrated in vacuo to give a residue. The residue was dissolved in 50 mL dichloromethane to give a solution, which was added to a solution of N,O-dimethylhydroxylamine hydrochloride (12.4 g, 126.9 mmol) and triethylamine (25.7 g, 253.9 mmol) in 100 mL dichloromethane, stirred at room temperature for another 1 h, concentrated, and purified by column chromatography to afford the desired product as a colorless oil (9.4 g, 73.8%).

Provenance & Evidence