Sodium Hydroxide → HCID 67041249, compound

Participants

Reaction Steps

A solution of ethoxyacetyl chloride (0.87 g, 7.1 mmol) in acetonitrile (10 mL) was added to a solution of N4-[(5-phenylisoxazol-3-yl)methyl]quinoline-3,4-diamine (2.05 g, 6.48 mmol) in acetonitrile (100 mL), and the solution was stirred at room temperature overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in 3:1 ethanol:water (100 mL). Solid sodium hydroxide (389 mg, 9.72 mmol) was added, and the solution was heated at reflux overnight. The ethanol was removed under reduced pressure, and the resultant aqueous solution was adjusted to pH 5 with the additional of dilute hydrochloric acid. The acidic solution was extracted several times with dichloromethane, and the combined organic fractions were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with 4% to 6% methanol in dichloromethane to provide 0.650 g of 2-(ethoxymethyl)-1-[(5-phenylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinoline as a white solid.

Provenance & Evidence