Sodium Hydroxide → 4-Oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid

HRID 400981노트

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HRID 400981 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]([F:15])([F:14])[F:13])[NH:5][CH:4]=[C:3]1[C:16]([O:18]CC)=[O:17].[OH-].[Na+]>[Pd]>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]([F:15])([F:13])[F:14])[NH:5][CH:4]=[C:3]1[C:16]([OH:18])=[O:17]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 21829730Ethyl 4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

생성물 1

HCID 156185574-Oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-184d5874a8bf4f2db9b7e4e51f5ac164
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741922B2

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