m-Chloroperbenzoic acid → HCID 67506771, compound

Participants

Reaction Steps

1-(Benzyloxy)-2-phenyl-1H-imidazo[4,5-c]quinoline (0.951 g, 2.71 mmol) was combined with 3-chloroperoxybenzoic acid (1.2 g of 77% pure material, 5.4 mmol) in dichloromethane (10 mL) and stirred at room temperature for 30 minutes. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the presence of starting material; additional 3-chloroperoxybenzoic acid (0.1 g) was added. The reaction mixture was stirred for 18 hours at room temperature and then diluted with dichloromethane, washed sequentially with saturated aqueous potassium carbonate, water, and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide 1.25 g of 1-(benzyloxy)-5-oxido-2-phenyl-1H-imidazo[4,5-c]quinoline as a black oil. Attempts to obtain a solid by trituration with hexane/diethyl ether and hexane were unsuccessful.

Provenance & Evidence