Xanthoxylin → 1-{4,6-Dimethoxy-2-[(6,7-dimethoxy-4-quinolyl)oxy]-phenyl}-1-ethanone

HRID 228548

반응식

HRID 228548 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][C:17]([C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([O:27][CH3:28])=[CH:21][C:20]=1[OH:29])=[O:18]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:28][O:27][C:22]1[CH:23]=[C:24]([O:25][CH3:26])[C:19]([C:17](=[O:18])[CH3:16])=[C:20]([O:29][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:21]=1

참가 물질

5

반응물 2

HCID 66654XanthoxylinHCID 4596104-Chloro-6,7-dimethoxyquinoline

생성물 1

HCID 577563651-{4,6-Dimethoxy-2-[(6,7-dimethoxy-4-quinolyl)oxy]-phenyl}-1-ethanone수율 27%

시약·촉매·용매 2

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

반응 조건

온도
120 °C

실험 절차

4-Chloro-6,7-dimethoxyquinoline (56 mg), 2-hydroxy-4,6-dimethoxyacetophenone (196 mg), and 4-dimethylaminopyridine (122 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 (25 mg, yield 27%).

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-2698dd9263034d84b4c14d37e94e58bd
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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