Picolinic acid → N-Methoxy-N-methylpicolinamide

Participants

Reaction Steps

Picolinic acid (12.3 g, 100 mmol), N,N-carbonyldiimidazole (17.8 g, 110 mmol) and anhydrous CH2Cl2 (150 mL) were combined and stirred at room temperature for 60 minutes. To the reaction mixture was added a solution of N,O-dimethylhydroxylamine hydrochloride (10.7 gr, 0.11 mole), anhydrous CH2Cl2 (50 mL) and diisopropylethylamine (20 mL), and stirring continued overnight. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel 60, MeOH/CH2Cl2, 9:1) to afford pyridine-2-carboxylic acid methoxy-methyl-amide (a pale yellow liquid, 15.9 g, 95%); ESI) m/z 167.

Provenance & Evidence