Water → HCID 86605661, compound

Participants

Reaction Steps

To a solution of 6-(2-hydroxyethoxy)-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.0 g, 2.8 mmol) in N,N-dimethylformamide (10 ml) was added sodium hydride (60% in oil, 0.14 g, 3.4 mmol), and the mixture was stirred at room temperature for 1 hr. tert-Butyl bromoacetate (1 ml, 6.8 mmol) was added to the reaction mixture and the mixture was stirred at room temperature for 17 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl (2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}ethoxy)acetate (0.9 g, yield 69%) as an oil.

Provenance & Evidence