4-Chloro-6,7-dimethoxyquinoline → HCID 22132659, compound

HRID 1857193Notes

Reaction equation

HRID 1857193 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][CH:20]=[C:19]2[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 12299673(3,4-Dichlorophenyl)(4-hydroxyphenyl)methanone

Product 1

HCID 22132659HCID 22132659, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 3,4-dichlorophenyl 4-hydroxyphenyl ketone (154 mg) obtained in Example 121 and 4-dimethylaminopyridine (77 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 3 hours. 4-Chloro-6,7-dimethoxyquinoline (129 mg) was added, and the admixture was refluxed with heat for 21 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by thin layer chromatography on silica gel eluting with hexane/acetone (2/1) to obtain 81 mg of the title compound (yield: 31%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 21 hours
  3. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  4. dry with materialthe chloroform layer was then dried with anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. distillationby reduced-pressure distillation
  7. customthe resulting residue was purified by thin layer chromatography on silica gel eluting with hexane/acetone (2/1)

Sources & evidence

ORD record
ord-b64980b6ab684b828b7e8a3b497e9b45
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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