4-Chloro-6,7-dimethoxyquinoline → (3-Trifluoromethylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone

HRID 1857208Notes

Reaction equation

HRID 1857208 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1.CCCCCC.C(OCC)(=O)C>COCCOCCOC>[F:19][C:16]([F:17])([F:18])[C:12]1[CH:11]=[C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[CH:3][CH:4]=2)=[O:9])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 21226206Ethyl acetate hexaneHCID 22132694(4-Hydroxyphenyl)[3-(trifluoromethyl)phenyl]methanone

Product 1

HCID 22132736(3-Trifluoromethylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanoneYield 28%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
160 °C

Procedure

Under argon, 3-trifluoromethylphenyl 4-hydroxyphenyl ketone (432 mg) obtained in Example 139 and 4-chloro-6,7-dimethoxyquinoline (363 mg) were dissolved in diethylene glycol dimethyl ether (10 ml), and the solution was then refluxed at 160° C. for 11 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate and then by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1) to obtain 204 mg of the title compound (yield: 28%).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  2. dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby reduced-pressure distillation
  5. customthe resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-02de19f6a93443cebff46c1afe9f4751
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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