Water → 1-{5-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-1-propanone

HRID 228562Notes

Reaction equation

HRID 228562 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[C:6]([CH:8]([OH:11])[CH2:9][CH3:10])[CH:7]=1.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 688291941-{5-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-1-propanol

Product 1

HCID 577563841-{5-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-1-propanoneYield 6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-{5-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-1-propanol was dissolved in anhydrous dimethylsulfoxide (1 ml), a sulfur trioxide trimethylamine complex (70 mg) was added to the solution at 0° C., and the mixture was stirred at room temperature for 18 hr. Water (1 ml) was added dropwise to the reaction solution to stop the reaction. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel using ethyl acetate-hexane for development to give the title compound (11 mg, yield 6%).

Workup

  1. additiona sulfur trioxide trimethylamine complex (70 mg) was added to the solution at 0° C.
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distillation under the reduced pressure
  8. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f596937879ea4fb4bacd3c23e642eea6
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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