Water → 5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide

Participants

Reaction Steps

To a solution of 5-bromo-nicotinic acid (100 g, 0.5 mol) in THF (2 L) at 0° C., (COCl)2 (95 g, 0.74 mol) was added. After stirring for 0.5 h, Et3N (152 g, 1.5 mol) and O, N-dimethyl hydroxylamine. HCl (140 g, 1.5 mol) were added. The reaction mixture was stirred at room temperature for 2.5 hours and then water (200 mL) and EtOAc (500 mL) were added. The organic layer was separated, dried (MgSO4) and concentrated in vacuo to afford 5—the title compound as a brown oil in 82% yield, 100%.

Provenance & Evidence