Dimethyl Sulfoxide → 4-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

HRID 1008319Notes

Reaction equation

HRID 1008319 reaction equation
[H-].[Na+].CS(C)=O.[NH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[C:10]([CH3:16])[CH:9]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1>O>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:15][C:11]1[C:10]([CH3:16])=[CH:9][C:8]([NH2:7])=[C:13]([CH3:14])[CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 765444-Amino-2,5-dimethylphenolHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (60 wt %, 0.36 g) was added to dimethyl sulfoxide (10 ml), and the mixture was stirred at 50° C. for 30 min and was then cooled to room temperature. 4-Amino-2,5-dimethylphenol (1.23 g) was added to the cooled mixture, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinoline (1.00 g) was added thereto, and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel by development with chloroform/acetone (1/1) to give the title compound.

Workup

  1. temperaturewas then cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 10 min
  3. stirringthe mixture was stirred at 100° C. overnight
  4. extractionfollowed by extraction with chloroform
  5. washThe chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by chromatography on silica gel by development with chloroform/acetone (1/1)

Sources & evidence

ORD record
ord-1e3154ff2ec24f94afa1827cab384c47
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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