4-Toluenesulfonyl chloride → HCID 58970368, compound

Participants

Reaction Steps

mCPBA (3.48 g, 15.1 mmol) was added to a solution of 3-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide (2.20 g, 8.65 mmol) in chloroform (100 mL). The reaction was stirred for two hours at ambient temperature and cooled to 0° C. Ammonium hydroxide (40 mL) was added followed by p-toluenesulfonyl chloride (3.21 g, 16.9 mmol), which was added over a period of five minutes. The reaction was stirred for two hours at ambient temperature and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 90:10 to 80:20). The resulting solid was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven at 60° C. to provide 0.145 g of 3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide as a off-white powder, mp 237-239° C.

Provenance & Evidence