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

HRID 228609노트

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HRID 228609 반응식
[F:1][C:2]1[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([OH:13])=[CH:4][CH:3]=1.Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][CH:16]=[C:15]2[O:13][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 2783185Ethyl 5-fluoro-2-hydroxybenzoate

생성물 1

HCID 57756435Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-fluorobenzoate수율 30.8%

시약·촉매·용매 2

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

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온도
120 °C

실험 절차

Ethyl 5-fluorosalicylate (191 mg), 4-chloro-6,7-dimethoxyquinoline (125 mg), and 4-dimethylaminopyridine (205 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 residue, 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, and the residue was purified by column chromatography using acetone-hexane to give the title compound (64 mg, yield 22%).

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 residue
  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-b5001a92107748159363ffd9dbc36665
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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