2-Methyl-2-butene → 3-(3-Methylisoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxylic acid

Participants

Reaction Steps

3-(3-methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carboxaldehyde (a) (16 mg, 0.05 mmol) was dissolved in tert-butanol (2 mL) followed by the sequential addition of saturated aqueous sodium phosphate monobasic solution (0.25 mL), 2-methyl-2-butene (0.05 mL), and sodium chlorite (NaClO2) (7 mg, 0.08 mmol). The mixture was stirred at room temperature for 3.5 h and concentrated. The residue was dissolved in ethyl acetate (15 mL), dried (MgSO4), filtered, and concentrated to give 3-(3-methylisoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxylic acid (b) as a white solid (17.3 mg, 100%). 1H NMR (300 MHz, CD3OD) δ 8.19 (dd, J=6.4, 8.0 Hz, 1H), 7.96 (d, J=6.4 Hz, 1H), 7.51-7.43 (m, 4H), 7.31-7.23 (m, 2H), 6.33 (s, 1H), 2.18 (s, 3H). MS: 347.2 (M+H).

Provenance & Evidence