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4-Chloro-6,7-dimethoxyquinoline → Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-(pyrrol-1-yl)benzoate

HRID 228622
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HRID 228622 반응식
[N:1]1([C:6]2[CH:16]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([OH:17])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][CH:20]=[C:19]2[O:17][C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078344Ethyl 5-(pyrrol-1-yl)salicylate

생성물 1

HCID 57756406Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-(pyrrol-1-yl)benzoate수율 22.1%

시약·촉매·용매 2

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

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온도
120 °C

실험 절차

Ethyl 5-(pyrrol-1-yl)salicylate (170 mg), 4-chloro-6,7-dimethoxyquinoline (87 mg), and 4-dimethylaminopyridine (143 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 (36 mg, yield 15%).

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-8525bcda652946ab90848e80930cac56
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560558B2

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