Sodium Hydroxide → HCID 66620914, compound

Participants

Reaction Steps

To a round-bottomed flask containing 3-[7-bromo-2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetate (15.7 g, 36.8 mmol) was added 2 N NaOH (300 mL) and the reaction was stirred at ambient temperature for 72 h. To the stirred reaction mixture was added additional 2 N NaOH (80 mL) and after 2 h more 2 N NaOH (100 mL) was added. After 1 h the reaction was diluted with water (1.1 L) and transferred to a separatory funnel. The aqueous layer was extracted with dichloromethane (3×800 mL). The aqueous layer was then extracted with ethyl acetate (3×800 mL) and the ethyl acetate extracts were combined, dried (MgSO4), filtered, and the solvent evaporated to afford a solid. The solid was washed with diethyl ether to afford 3-bromo-10,11-dihydro-9H-[1,3]oxazino[3′,2′:1,2]imidazo[4,5-c]quinoline (3.41 g) as a white solid. The dichloromethane extracts were combined and concentrated under reduced pressure. The residue was treated with 2 N NaOH to afford additional product.

Provenance & Evidence