Benzyl Bromide → HCID 18760176, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, sodium hydride (16.88 g of 60% in mineral oil, 422 mmol) was added in portions to a solution of 2-(1H-imidazo[4,5-c]quinolin-1-yl)ethanol (60.0 g, 281 mmol) in anhydrous N,N-dimethylformamide (600 mL). The alkoxide was allowed to stir for about 1.5 hours. Benzyl bromide (50.2 mL, 422 mmol) was slowly added over a period of about 30 minutes. The reaction mixture was allowed to stir at ambient temperature overnight. Solvent was removed under reduced pressure. The residue was taken up in ethyl acetate, washed several times with water, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide 1-[2-(benzyloxy)ethyl]-1H-imidazo[4,5-c]quinoline as a dark oil.

Provenance & Evidence