Dichloromethane → N-(2-benzoyl-4-chlorophenyl)-2-(3-tert-butyl-isoxazol-5-yl)-acetamide

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of but-3-ynoic acid (2-benzoyl-4-chlorophenyl)amide (a) (0.100 g, 0.336 mmol) in anhydrous DCM (7 mL) was added 2,2-dimethylpropionaldehyde oxime (0.204 g, 2.02 mmol) and sodium hypochlorite solution (3.50 mL). After stirring for 2 h at 0° C., the reaction was warmed to 25° C. and stirred overnight. The organic layer was separated, dried (MgSO4), and concentrated to provide N-(2-benzoyl-4-chlorophenyl)-2-(3-tert-butyl-isoxazol-5-yl)-acetamide as a yellow oil. This ketoamide was dissolved in anhydrous toluene (4 mL) and treated with triethylamine (0.5 mL). After stirring for 12 h at 25° C., the reaction mixture was evaporated to afford the crude product as a yellow oil. Purification by flash chromatography afforded 3-(3-tert-butyl-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (b) (0.10 g, 77% yield) as a white solid. 1H NMR (300 MHz, CDCl3): δ 11.83 (s, 1H), 7.52-7.45 (m 4H), 7.36 (d, J=8.6 Hz, 1H), 7.26-7.20 (m, 3H), 6.42 (s, 1H), 1.26 (s, 9H). MS: 379 (M+H).

Provenance & Evidence