Benzyl Bromide → HCID 68830882, compound

Participants

Reaction Steps

To a solution of 6-hydroxy-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.5 g, 4.7 mmol) and benzyl bromide (0.61 g, 5.1 mmol) in N,N-dimethylformamide (10 ml) was added potassium carbonate (0.71 g, 5.1 mmol), and the mixture was stirred at room temperature for 17 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (100 ml). The aqueous layer was separated and extracted with ethyl acetate (50 ml). The organic layer and the extract were combined and the mixture was washed with saturated brine (50 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography, and crystallized from n-hexane-ethyl acetate to give 6-(benzyloxy)-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.7 g, yield 91%) as pale-yellow crystals.

Provenance & Evidence