4-Chloro-6,7-dimethoxyquinoline → HCID 22132765, compound

HRID 1857197Notes

Reaction equation

HRID 1857197 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:9].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:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:9])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 22132708(4-Hydroxyphenyl)(2-methylphenyl)methanone

Product 1

HCID 22132765HCID 22132765, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 4-hydroxyphenyl 2-methylphenyl ketone (1.334 g) obtained in Example 126 and 4-dimethylaminopyridine (845 mg) were added to xylene (15 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (1.406 g) was added, and the admixture was refluxed with heat for 23 hours. 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, followed by thin layer chromatography on silica gel eluting with hexane/acetone (2/1), to obtain 1.258 g of the title compound (yield: 50%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 23 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 chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-d95578ef33b149d88aa3984206e241be
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…