Hydrochloric Acid → 2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamine

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Reaction Steps

HCl in ethanol (3M, 75 mL) was added to tert-butyl [2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]carbamate (5.07 g, 10.04 mmol) and the solution was heated at reflux for 15 minutes. The volatiles were removed under reduced pressure and the orange residue was partitioned between dilute aqueous hydrochloric acid and dichloromethane. The aqueous layer was washed with 2 portions of dichloromethane and then made basic with the addition of aqueous ammonium hydroxide. The aqueous fraction was then extracted with three portions of dichloromethane. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to yield 3.77 g of 2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamine as a brown oil.

Provenance & Evidence