Hydrochloric Acid → HCID 58833621, compound

Participants

Reaction Steps

Concentrated hydrochloric acid (8.5 mL) was added to a solution of tert-butyl 3-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate (prepared as described in Example 393, 12 g, 26 mmol) in ethanol (300 mL). The solution was heated at reflux for 4 hours. Upon cooling to ambient temperature a precipitate formed. The solid was isolated by filtration and the filtrate was evaporated to afford a white solid. The solids were combined and dissolved in water (40 mL). The solution was adjusted to approximately pH 12 with 50% aqueous sodium hydroxide and then was extracted with dichloromethane (4×250 mL). The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated to yield a solid that was purified by trituration in hot acetonitrile to provide 6.5 g of 7-(3-aminopropoxy)-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as yellow crystals, mp 165-166.5° C.

Provenance & Evidence