Potassium Hydroxide → 6-Fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245229노트

반응식

HRID 245229 반응식
[OH-:1].[K+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][CH3:25])[CH:20]=[CH:21][CH:22]=1>O.C(O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:27])[F:28])[CH:18]=1)[C:24]([CH3:25])=[C:7]2[C:8]([OH:13])=[O:1]

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 137064Propiophenone, 3'-(trifluoromethyl)HCID 2365665-Fluoroisatin

생성물 1

HCID 673838086-Fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid수율 100.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Potassium hydroxide (20.39 g, 363 mmol) in water (40 mL) was added to a suspension of 5-fluoro-1H-indole-2,3-dione (10.0 g, 60.6 mmol) in ethanol (100 mL) slowly. 1-[3-(Trifluoromethyl)phenyl]-1-propanone (12.24 g, 60.6 mmol) was added, and the mixture was heated to reflux for 1 h. The solvent was removed under reduced pressure, the residue was dissolved in water, and the mixture was washed with ether (3 times). The aqueous mixture was chilled and adjusted to pH˜3 with concentrated HCl. The solid was collected by filtration, washed with water, and air dried to afford 6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (21.2 g, >99% yield). MS (m/z) 350.1 (M+H+).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washthe mixture was washed with ether (3 times)
  6. temperatureThe aqueous mixture was chilled
  7. filtrationThe solid was collected by filtration
  8. washwashed with water, and air
  9. customdried

출처 및 근거

ORD 기록
ord-9efed4f656244defa2cf9c287b7caa9f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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