4-Chloro-6,7-dimethoxyquinoline → HCID 22132803, compound

HRID 1857235Notes

Reaction equation

HRID 1857235 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=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:14]=[CH:15][C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 13453359(4-Hydroxyphenyl)(4-iodophenyl)methanone

Product 1

HCID 22132803HCID 22132803, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 4-hydroxyphenyl 4-iodophenyl ketone (380 mg) obtained in Example 177 and 4-dimethylaminopyridine (158 mg) were added to xylene (11 ml), and the admixture was stirred at room temperature. After 2 hours, 4-chloro-6,7-dimethoxyquinoline (262 mg) was added, and the admixture was refluxed with heat overnight. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was then 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 with chloroform/ethyl acetate, followed by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1), to obtain 459 mg of the title compound (yield: 77%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat overnight
  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 chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-4e351e87a0954edca7cf2923e57f672c
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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