Dimethyl Sulfoxide → 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

HRID 1008317Notes

Reaction equation

HRID 1008317 reaction equation
[H-].[Na+].CS(C)=O.Cl.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[Cl:16].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>[Cl:16][C:10]1[CH:11]=[C:12]([O:15][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH:13]=[CH:14][C:9]=1[NH2:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 125981904-Amino-3-chlorophenol hydrochloride

Product 1

HCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroanilineYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (60 wt %, 0.72 g) was added to dimethyl sulfoxide (10 ml). The mixture was stirred at 50° C. for 30 min and was then cooled to room temperature. 4-Amino-3-chlorophenol hydrochloride (1.61 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 methanol was added to the residue. The precipitated crystal was collected by suction filtration to give 0.89 g (yield 60%) of 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, and methanol
  8. additionwas added to the residue
  9. filtrationThe precipitated crystal was collected by suction filtration

Sources & evidence

ORD record
ord-86da845f668d4e40883b04d148feeb02
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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