Ammonium Hydroxide → HCID 57447012, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated ammonium hydroxide (8.0 mL of 29%) was added to a solution of ethyl 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanoate (5.1 g, 16 mmol) in 2-methyltetrahydrofuran (10 mL), and the mixture was heated overnight in a sealed high-pressure vessel at 80° C. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the reaction was incomplete. The solvents were evaporated under a stream of nitrogen, and ammonium acetate (10 g) was added. The vessel was sealed and heated overnight at 135° C. The reaction was allowed to cool to ambient temperature, and water (50 mL) was added. The mixture was filtered, and the filtrate was washed with saturated aqueous sodium bicarbonate (25 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 2.95 g of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide as a light brown solid.

Provenance & Evidence