Hydrochloric Acid → HCID 86052969, compound

Participants

Reaction Steps

Concentrated hydrochloric acid (8 mL) was added to a mixture of 7-bromo-1-(4,4-dimethoxybutyl)-2-propyl-1H-imidazo[4,5-c]quinoline (57.0 g, 140.3 mmol) in THF (250 mL) and water (70 mL) and stirred overnight at ambient temperature. Additional concentrated hydrochloric acid (10 mL) was added and the reaction mixture was stirred for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water and neutralized with saturated aqueous sodium bicarbonate solution. The mixture was diluted with 10% methanol in dichloromethane, the phases were separated, and the combined organics were dried over magnesium sulfate and concentrated under reduced pressure to afford 50.3 g of 4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde.

Provenance & Evidence