4-Chloro-6,7-dimethoxyquinoline → (2-Trifluoromethylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone

HRID 1857214Notes

Reaction equation

HRID 1857214 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])=[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>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[F:19][C:16]([F:17])([F:18])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:3][CH:4]=1)=[O:9]

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 221326192-Trifluoromethylphenyl 4-hydroxyphenyl ketone

Product 1

HCID 22132725(2-Trifluoromethylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanoneYield 55.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 2-trifluoromethylphenyl 4-hydroxyphenyl ketone (959 mg) obtained in Example 145 and 4-dimethylaminopyridine (484 mg) were added to xylene (7 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (805 mg) was added, and the admixture was then refluxed with heat overnight. The reaction mixture was treated in the same manner as described in Example 130 to obtain 899 mg of the title compound (yield: 55%).

Workup

  1. temperaturethe admixture was then refluxed
  2. temperaturewith heat overnight
  3. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-847e6bd1312f481ca9e706ea76f11346
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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