Triethylamine → 6-(Methoxy-methyl-carbamoyl)-nicotinic acid methyl ester

Participants

Reaction Steps

A solution of pyridine-2,5-dicarboxylic acid-5-methyl ester (1.0 g, 5.52 mmol), 1,1′-carbonyldiimidazole (0.984 g, 6.07 mmol), 1,2-dichloroethane (30.0 mL) and DMF (8.0 mL) was stirred at room temperature for 1 hour. To the reaction mixture was added N,O-dimethylhydroxylamine hydrochloride (0.535 g, 5.52 mmol) and triethylamine (1.15 mL, 8.28 mmol) and stirred at room temperature for 12 hours. The reaction was diluted with dichloromethane (20.0 mL) and washed with water, 0.5N HCl and saturated NaHCO3, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (1.0 g, 81% yield).

Provenance & Evidence