Acetic Anhydride → HCID 58869121, compound

Participants

Reaction Steps

Acetic anhydride (0.490 mL, 5.14 mmol) and triethylamine (2.86 mL, 20.6 mmol) were added to a solution of 1-[4-(hydroxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride (1.80 g, 5.14 mmol) in dichloromethane (50 mL). The reaction mixture was stirred at room temperature for 2 hours, then 10% aqueous sodium hydroxide was added. The mixture was stirred for 1 hour, then was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, gradient elution with 10-20% methanol in dichloromethane). The appropriate fractions were combined and concentrated under reduced pressure to afford a solid that was slurried in 1:1 saturated aqueous sodium bicarbonate/water, filtered, washed with water, and dried to yield N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-hydroxyacetamide as brown needles, mp 191-193° C.

Provenance & Evidence