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

HRID 1857202Notes

Reaction equation

HRID 1857202 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=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>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[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:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[O:9])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 22132621(4-Hydroxyphenyl)(3-methylphenyl)methanone

Product 1

HCID 22132753{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}(3-methylphenyl)methanoneYield 45.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 4-hydroxyphenyl 3-methylphenyl ketone (307 mg) obtained in Example 132 and 4-dimethylaminopyridine (194 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (324 mg) was added, and the admixture was then refluxed with heat for 23 hours. The reaction mixture was treated in the same manner as described in Example 122 to obtain 262 mg of the title compound (yield: 45%).

Workup

  1. temperaturethe admixture was then refluxed
  2. temperaturewith heat for 23 hours
  3. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-c1850388ecb6446b89fcabf56ebe3d03
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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