1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → [2-(7-Benzyloxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]-ethanone

HRID 228906

반응식

HRID 228906 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12])=[O:3].[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([O:12][C:5]3[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=3[C:2](=[O:3])[CH3:1])=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 2

HCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-oneHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

생성물 1

HCID 23156581[2-(7-Benzyloxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]-ethanone수율 59%

시약·촉매·용매 2

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

반응 조건

온도
180 °C

실험 절차

2-Hydroxy-5-methoxyacetophenone (3.00 g), 7-benzyloxy-4-chloro-6-methoxyquinoline (6.65 g), and 4-dimethylaminopyridine (4.90 g) were suspended in o-dichlorobenzene (30 ml), and the suspension was stirred at 180° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 1-[2-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-ethanone (2.53 g, yield 59%).

후처리

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

출처 및 근거

ORD 기록
ord-0e4d680ea74640979d2e5a29d86407a8
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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