Sodium Hydroxide → HCID 68830457, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(aminomethyl)-2-isobutyl-4-phenylquinoline-6-carbonitrile (0.11 g, 0.35 mmol) in dimethyl sulfoxide (4 ml) was added 1N aqueous sodium hydroxide solution (2 ml) and the mixture was stirred at 80° C. for 3 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and 1N aqueous sodium hydroxide solution (50 ml) and the aqueous layer was extracted 4 times with ethyl acetate (50 ml). The organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by preparative HPLC. The objective fractions were combined and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (25 ml)-tetrahydrofuran (25 ml) and 1N aqueous sodium hydroxide solution (25 ml). The organic layer was washed with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from diisopropyl ether-ethyl acetate to give the title compound (0.043 g, yield 37%) as pale-yellow crystals.

Provenance & Evidence