4-Toluenesulfonyl chloride → HCID 58970357, compound

Participants

Reaction Steps

mCPBA (8.95 g, 38.9 mmol) was added to a solution of 3-(1H-imidazo[4,5-c]quinolin-1-yl)-N-methylpropanamide (4.4 g, 15.6 mmol) in chloroform (100 mL); the reaction was stirred for one hour at ambient temperature. Ammonium hydroxide (40 mL) was added, and the mixture was stirred vigorously for 15 minutes. p-Toluenesulfonyl chloride (5.94 g, 31.2 mmol) was added over a period of ten minutes, and the reaction was stirred for two hours. The reaction mixture was filtered to remove a precipitate, and the organic layer was separated and washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from methanol to provide 0.535 g of 3-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-N-methylpropanamide as off-white needles, mp>260° C.

Provenance & Evidence