Dimethylformamide → 5-Bromo-1-methylpyridin-2(1H)-one

Participants

Reaction Steps

With cooling with ice, potassium carbonate (5.96 g, 43.1 mmol) and methyl iodide (1.29 mL, 20.7 mmol) were added to a dimethylformamide (50 mL) solution of 5-bromo-2-hydroxypyridine (3.0 g, 7.24 mmol), and stirred at that temperature for 16 hours. Water was added to the reaction mixture, and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, ethyl acetate/hexane=1/1) to obtain the entitled compound (2.92 g, 90%) as a colorless oil.

Provenance & Evidence