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

HRID 720964ノート

反応式

HRID 720964 の反応式
[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]

参加物

5

反応物 2

HCID 218900064-(2-Methyl-4-nitrophenoxy)-6,7-dimethoxyquinolineHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 86593454ethyl acetate N,N-dimethylformamide triethylamine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5936433ccaf14d88994fa60e9e1dac0e
出典データセット
uspto-grants-2006_11
特許番号
US07135466B2

反応ノート

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