5-Bromoisatin → 6-Bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245239

반응식

HRID 245239 반응식
[OH-:1].[K+].[Br: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:22]=[CH:21][C:20]([C:23](=O)[CH2:24][CH3:25])=[CH:19][CH:18]=1>O.C(O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:27])[F:28])=[CH:22][CH:21]=1)[C:24]([CH3:25])=[C:7]2[C:8]([OH:13])=[O:1]

참가 물질

6

반응물 3

HCID 68895-BromoisatinHCID 14797Potassium HydroxideHCID 136554p-Trifluoromethylpropiophenone

생성물 1

HCID 673836206-Bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid수율 98%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A solution of potassium hydroxide (13.08 g, 233 mmol) in water (25.2 mL) was added slowly to a solution of 5-bromo-1H-indole-2,3-dione (9.76 g, 38.9 mmol) in ethanol (63.1 mL). 1-[4-(trifluoromethyl)phenyl]-1-propanone (8.64 g, 42.7 mmol) was added and the mixture was heated to reflux for 1 h. The reaction mixture was concentrated to remove the solvent, the residue was dissolved in water, and the mixture was washed three times with Et2O. The aqueous mixture was chilled, and concentrated HCl was added until the solution was pH 3. The solid was collected by filtration, washed with water, and dried under reduced pressure in a water bath at 100° C. The product was obtained as a light brown powder (15.6 g, 98%). This material was used without further purification. MS (m/z) 412.0 (M+H+).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. customto remove the solvent
  5. dissolutionthe residue was dissolved in water
  6. washthe mixture was washed three times with Et2O
  7. temperatureThe aqueous mixture was chilled
  8. additionconcentrated HCl was added until the solution
  9. filtrationThe solid was collected by filtration
  10. washwashed with water
  11. customdried under reduced pressure in a water bath at 100° C

출처 및 근거

ORD 기록
ord-cf262dca2b0949e48e17846215830107
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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