Sodium Hydroxide → 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid

Participants

Reaction Steps

A solution of sodium hydroxide (2.23 g, 55.9 mmol) in water (100 mL) was added to a solution of ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (14.6 g, 43.0 mmol) in ethanol (100 mL), and the reaction was stirred at ambient temperature overnight, concentrated to remove ethanol, and washed with dichloromethane. The resulting solution was adjusted to pH 5 with the addition of 10% hydrochloric acid. The mixture was extracted twice with chloroform, and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 11.5 g of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid.

Provenance & Evidence