HCID 19592412, compound → HCID 19592718, compound

Participants

Reaction Steps

To a solution of 3-bromo-4-carboxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (130 mg) in dry tetrahydrofuran was added 10M solution of borane-methyl sulfide complex in tetrahydrofuran (0.286 ml) at ambient temperature, and the mixture was stirred for 4 hours at the same temperature. The mixture was quenched by 1N hydrochloric acid and stirred for 1 hour at the same temperature. The mixture was extracted with ethyl acetate, and the extract was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate: n-hexane, 1:2, v/v) and crystallized from ethyl acetate-n-hexane to give 3-bromo-8-(2,6-dichlorobenzoylamino)-4-(2-hydroxyethyl)quinoline (68.4 mg).

Provenance & Evidence