Methanol → HCID 57538825, compound

Participants

Reaction Steps

Trichloroacetyl isocyanate (3.3 mL, 28 mmol) was added to a solution of 2-isopropyl-1-methoxy-5-oxido-1H-imidazo[4,5-c]quinoline (4.7 g, 118 mmol) in dichloromethane (100 mL), and the reaction was stirred three hours at room temperature. Methanol (20 mL) was added, and the mixture was stirred for 15 minutes and concentrated under reduced pressure. The residue was dissolved in methanol (25 mL), and sodium methoxide (0.5 mL of a 4.5 N solution in methanol) was added. The mixture was stirred at room temperature for three days and concentrated under reduced pressure. The residue was stirred with dichloromethane (25 mL). A solid was present and was collected by filtration, recrystallized from methanol/water, and dried overnight in a vacuum oven at 70° C. to provide 0.878 g of 2-isopropyl-1-methoxy-1H-imidazo[4,5-c]quinolin-4-amine as tan needles, mp 217-219° C.

Provenance & Evidence