反应详情

温度

0 °C

To a solution of 2-oxo-1,2-dihydropyridine-3-carboxylic acid (1.00 g, 7.18 mmol) in anhydrous tetrahydrofuran (40 mL) was added 4-methyl morpholine (1.01 g, 10.06 mmol). After cooling to 0° C., isobutyl chloroformate (1.27 g, 9.34 mmol) was added to the reaction mixture. The mixture was stirred at ambient temperature for 6 hours followed by the addition of aniline (0.87 g, 9.34 mmol). The resulting mixture was stirred at ambient temperature for 16 hours. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), and washed with saturated aqueous sodium bicarbonate (2×50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a colorless solid (1.50 g, 97%): 1H NMR (300 MHz, DMSO-d6) δ 12.71 (br s, 1H), 12.14 (s, 1H), 8.46-8.38 (m, 1H), 7.80-7.52 (m, 1H), 7.65-7.62 (m, 2H), 7.35-7.29 (m, 2H), 7.10-6.95 (m, 1H), 6.58-6.45 (m, 1H); MS (ES+) m/z 215.2 (M+1).

1. stirringThe resulting mixture was stirred at ambient temperature for 16 hours
2. customThe solvent was removed in vacuo
3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
4. washwashed with saturated aqueous sodium bicarbonate (2×50 mL) and brine (50 mL)
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo