4-(2-Methyl-4-nitrophenoxy)-6,7-dimethoxyquinoline → 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline

HRID 720964노트

반응식

HRID 720964 반응식
[CH3:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[H][H]>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C.[OH-].[Pd+2].[OH-]>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:2]=1[CH3:1]

참가 물질

5

반응물 2

HCID 218900064-(2-Methyl-4-nitrophenoxy)-6,7-dimethoxyquinolineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 218911624-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline수율 105.6%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 86593454ethyl acetate N,N-dimethylformamide triethylamine용매

실험 절차

4-Chloro-6,7-dimethoxyquinazoline (5.00 g) and 4-nitro-2-methylphenol (6.85 g) were suspended in monochlorobenzene (25 ml) to prepare a suspension which was then heated under reflux overnight. The solvent was removed by distillation under the reduced pressure. The residue was washed with ethyl acetate, was filtered, and was dried. Next, the resultant crystal was suspended in an aqueous sodium hydroxide solution to prepare a suspension. The suspension was then filtered, followed by drying to give 6.89 g of 4-(2-methyl-4-nitrophenoxy)-6,7-dimethoxyquinoline. 4-(2-Methyl-4-nitrophenoxy)-6,7-dimethoxyquinoline (1.36 g) was dissolved in ethyl acetate/N,N-dimethylformamide/triethylamine (25 ml/25 ml/5 ml). Palladium hydroxide (0.4 g) was added to the solution, and the mixture was stirred in a hydrogen atmosphere at room temperature overnight. After filtration through Celite, the solvent was removed by distillation under the reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure to give the title compound (1.31 g, yield 91%).

후처리

  1. filtrationAfter filtration through Celite
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure

출처 및 근거

ORD 기록
ord-5936433ccaf14d88994fa60e9e1dac0e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135466B2

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