2-Propenylphenol → 6,7-Dimethoxy-4-[2-(1-propenyl)phenoxy]quinoline

HRID 228507

반응식

HRID 228507 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.[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])=[CH:17][CH3:18]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH:16]=[CH:17][CH3:18]

참가 물질

5

반응물 2

HCID 930292-PropenylphenolHCID 4596104-Chloro-6,7-dimethoxyquinoline

생성물 1

HCID 688300666,7-Dimethoxy-4-[2-(1-propenyl)phenoxy]quinoline수율 43%

시약·촉매·용매 2

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

반응 조건

온도
140 °C

실험 절차

4-Chloro-6,7-dimethoxyquinoline (100 mg), 2-(1-propenyl)phenol (231 μl), and 4-dimethylaminopyridine (220 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 140° C. for 7 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Thereafter, water was 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 (137 mg, yield 43%).

후처리

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

출처 및 근거

ORD 기록
ord-a52adc89b48246fda8d251cbb92b06a7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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