Ammonia → HCID 68829543, compound

Participants

Reaction Steps

To a mixture of 2-{[3-cyano-4-(2-fluorophenyl)-2-isobutylquinolin-6-yl]oxy}acetamide (0.11 g, 0.29 mmol), 25% aqueous ammonia (2 ml), tetrahydrofuran (2 ml) and methanol (10 ml) was added Raney-nickel (1 ml), and the mixture was stirred under a hydrogen (0.5 MPa) atmosphere at room temperature for 6 hrs. The reaction mixture was filtered, and the filtrate was partitioned between ethyl acetate (50 ml) and 10% aqueous potassium carbonate solution (25 ml). The organic layer was washed with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give a colorless oil. This was dissolved in ethyl acetate (2 ml) and 4N solution of hydrogen chloride in ethyl acetate (1 ml) was added. The reaction mixture was concentrated and the obtained crude crystals were recrystallized from diisopropyl ether-methanol to give the title compound (0.078 g, yield 59%) as pale-yellow crystals.

Provenance & Evidence