Potassium Hydroxide → HCID 58970366, compound

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (15 mL of a 1 N solution in dichloromethane) was added to a solution of 3-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide (1.1 g, 3.2 mmol, Example 28) in 1,2-dichloroethane (35 mL). The reaction was heated at reflux for 35 minutes, cooled to approximately 0° C., and adjusted to pH 8 with the addition of a solution of potassium hydroxide (90 mL of a 0.5 N solution in methanol). The volatiles were removed under reduced pressure, and the residue was mixed with methanol (50 mL) and isolated by filtration. The filtrate was concentrated under reduced pressure, and the residue was stirred overnight with saturated aqueous sodium bicarbonate (35 mL). The resulting solid was isolated by filtration, combined with material from another run, and purified by column chromatography on silica gel (eluting with 20% methanol in dichloromethane containing 1% ammonium hydroxide) and dried in a vacuum oven for three hours at 60° C. to provide 3-[4-amino-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide as white crystals, mp 201-203° C.

Provenance & Evidence