Ammonia → HCID 58970360, compound

Participants

Reaction Steps

A modification of the methods described in Part C of Example 60 was used to treat methyl 3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate (7.6 g, 21 mmol) with potassium hydroxide (44 mL of 0.5 M); additional potassium hydroxide (22 mL) was added after refluxing for four hours. After the reaction was heated at reflux for five days, additional potassium hydroxide (11 mL) was added, and the reaction was heated for four more hours. After the reaction with oxalyl chloride (3.7 mL, 42 mmol) was stirred overnight, additional oxalyl chloride (1.0 mL) was added, and then the reaction was stirred for two hours. After the addition of ammonia in methanol (35 mL), the reaction was stirred for one hour and then concentrated. The residue was stirred with saturated aqueous sodium bicarbonate for 30 minutes, isolated by filtration, and recrystallized three times from methanol/water. During the first recrystallization, a solution in methanol was filtered through a 20 micron filter prior to the addition of water. The resulting crystals were dried overnight in a vacuum oven at 70° C. to provide 1.60 g of 3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide as light tan crystals, mp 231-233° C.

Provenance & Evidence