4-Chloro-6,7-dimethoxyquinoline → Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-(2,4-difluorophenyl)benzoate

HRID 228620

반응식

HRID 228620 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:19]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([OH:20])=[CH:11][CH:10]=1.Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[CH:24][CH:23]=[C:22]2[O:20][C:12]1[CH:11]=[CH:10][C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

5

반응물 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078331Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

생성물 1

HCID 57756448Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-(2,4-difluorophenyl)benzoate수율 24%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 72391,2-Dichlorobenzene용매

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온도
120 °C

실험 절차

Ethyl 5-(2,4-difluorophenyl)salicylate (188 mg), 4-chloro-6,7-dimethoxyquinoline (57 mg), and 4-dimethylaminopyridine (93 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give the title compound (13 mg, yield 24%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the reaction solution
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-5b1485f1413d4bbda7b3af624a1e565c
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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