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4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- → 6-Benzyloxy-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline

HRID 229018
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HRID 229018 반응식
[OH:1][C:2]1[C:3]([CH3:15])=[N:4][C:5]2[C:10]([C:11]=1C(O)=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:16]([O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[N:30]=[CH:29][CH:28]=[C:27]2Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH2:16]([O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[N:30]=[CH:29][CH:28]=[C:27]2[O:1][C:2]1[C:3]([CH3:15])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

5

반응물 2

HCID 670244-Quinolinecarboxylic acid, 3-hydroxy-2-methyl-HCID 230227816-(Benzyloxy)-4-chloro-7-methoxyquinoline

생성물 1

HCID 230784416-Benzyloxy-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline수율 63%

시약·촉매·용매 2

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

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온도
150 °C

실험 절차

3-Hydroxy-2-methyl-4-quinoline carboxylic acid (549 mg), 6-benzyloxy-4-chloro-7-methoxyquinoline (810 mg), and 4-(N,N-dimethylamino)-pyridine (990 mg) were dissolved in 1,2-dichlorobenzene (40 ml) to prepare a solution. The mixture was stirred at 150° C. overnight. 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 washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-acetone to give the title compound (718 mg, yield 63%).

후처리

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

출처 및 근거

ORD 기록
ord-8d3c988bb38246bea1b5dbe58048b442
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560558B2

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