m-Chloroperbenzoic acid → 1-ethoxy-5-oxido-1H-imidazo[4,5-c]quinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 1-ethoxy-1H-imidazo[4,5-c]quinoline (2.45 g, 11.5 mmol) in dichloromethane (100 mL) was cooled to approximately 0° C., and 3-chloroperoxybenzoic acid (3.85 g of approximately 77% pure material, 17 mmol) was added. The reaction was stirred for ten minutes at 0° C., stirred for three hours at room temperature, and then stirred with saturated aqueous sodium bicarbonate (35 mL) for 15 minutes. The aqueous layer was separated and extracted with dichloromethane (5×50 mL), and the combined organic fractions were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 2.4 g of 1-ethoxy-5-oxido-1H-imidazo[4,5-c]quinoline as an orange solid.

Provenance & Evidence