Water → 3-[7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetate

Participants

Reaction Steps

To a round-bottomed flask containing 3-(7-bromo-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propyl acetate (28.9 g, 76.0 mmol) was added water (180 mL), ethanol (180 mL), and ammonium hydroxide (38 mL). The resulting suspension was stirred at ambient temperature. To this suspension was added iodomethane (9.5 mL, 152 mmol), and the reaction was stirred for 2 h. The suspension was filtered through a sintered glass funnel and the residue was washed with diethyl ether and dried under reduced pressure to afford 3-[7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetate (22.2 g) as tan solid.

Provenance & Evidence