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

HRID 228629
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HRID 228629 반응식
[C:1]([C:4]1[CH:15]=[C:8]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[C:7]([OH:16])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:16][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:15][C:8]=1[C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10]
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참가 물질

5

반응물 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078328Propyl 5-acetylsalicylate

생성물 1

HCID 57756400Propyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-acetylbenzoate수율 18.9%

시약·촉매·용매 2

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

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온도
120 °C

실험 절차

Propyl 5-acetylsalicylate (202 mg), 4-chloro-6,7-dimethoxyquinoline (101 mg), and 4-dimethylaminopyridine (164 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. The residue was purified by column chromatography using acetone-hexane to give the title compound (35 mg, yield 9%).

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-0e0c4e37f57f459d8ebd25c4fd2d5b6f
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560558B2

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