反应详情

温度

80 °C

Ethyl 4-oxo-5-(trifluoromethyl)-1H-quinoline-3-carboxylate (6) (58 g, 0.2 mol, crude reaction slurry containing Pd/C) was suspended in NaOH (814 mL of 5 M, 4.1 mol) in a 1 L flask with a reflux condenser and heated at 80° C. for 18 h, followed by further heating at 100° C. for 5 h. The reaction was filtered warm through packed Celite to remove Pd/C and the Celite was rinsed with 1 N NaOH. The filtrate was acidified to about pH 1 to obtain a thick, white precipitate. The precipitate was filtered, then rinsed with water and cold acetonitrile. The solid was then dried under vacuum to provide 4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid (7) as a white solid. 1H NMR (400.0 MHz, DMSO-d6) δ 15.26 (s, 1H), 13.66 (s, 1H), 8.98 (s, 1H), 8.13 (dd, J=1.6, 7.8 Hz, 1H), 8.06-7.99 (m, 2H).

1. temperatureby further heating at 100° C. for 5 h
2. filtrationThe reaction was filtered
3. temperaturewarm
4. customto remove Pd/C
5. washthe Celite was rinsed with 1 N NaOH
6. customto obtain a thick, white precipitate
7. filtrationThe precipitate was filtered
8. washrinsed with water and cold acetonitrile
9. customThe solid was then dried under vacuum