Triethylamine → N-methoxy-N,1-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxamide

Participants

Reaction Steps

A suspension of 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (540 mg, 1.0 eq), EDCI (811 mg, 1.2 eq) and HOBt (572 mg, 1.2 eq) in 20 mL CH2Cl2 was stirred at r.t. for 5 min Then N-methoxymethanamine hydrochloride (413 mg, 1.2 eq) and Et3N (1.1 g, 3.0 eq) were added, and the reaction was stirred at rt overnight. Water was added, and the mixture was extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (555 mg, 80% yield). 1H NMR (400 MHz, CDCl3) δ 7.32 (d, J=6.8 Hz, 1H), 6.78 (s, 1H), 6.32 (dd, J=6.8 Hz, 1.6 Hz, 1H), 3.61 (s, 3H), 3.57 (s, 3H), 3.32 (s, 3H).

Provenance & Evidence