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

HRID 720964Notes

Reaction equation

HRID 720964 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 86593454ethyl acetate N,N-dimethylformamide triethylamineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-5936433ccaf14d88994fa60e9e1dac0e
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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