2-Methyl-4-nitrophenol → 4-(2-Methyl-4-nitrophenoxy)-6,7-dimethoxyquinoline

HRID 720963Notes

Reaction equation

HRID 720963 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4]N=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)([O-:18])=[O:17].Cl[C:28]1C=CC=CC=1>>[CH3:26][C:21]1[CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=[CH:23][C:22]=1[O:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:28]=1

Participants

4

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 7964ChlorobenzeneHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 218900064-(2-Methyl-4-nitrophenoxy)-6,7-dimethoxyquinoline

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. customto prepare a suspension which
  2. temperaturewas then heated
  3. temperatureunder reflux overnight
  4. customThe solvent was removed by distillation under the reduced pressure
  5. washThe residue was washed with ethyl acetate
  6. filtrationwas filtered
  7. customwas dried
  8. customto prepare a suspension
  9. filtrationThe suspension was then filtered
  10. customby drying

Sources & evidence

ORD record
ord-5d8ba0259c0842ecb1f13545f0613fa0
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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