4-Chloro-6,7-dimethoxyquinoline → HCID 22132734, compound

HRID 1857199Notes

Reaction equation

HRID 1857199 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[O:11])=[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>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:10]([C:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)=[O:9])=[O:11]

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 22132746HCID 22132746, compound

Product 1

HCID 22132734HCID 22132734, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 2-furoyl 4-hydroxyphenyl ketone (205 mg) obtained in Example 129 and 4-dimethylaminopyridine (146 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (244 mg) was added, and the admixture was then refluxed with heat for 20 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was 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 chloroform/ethyl acetate (5/1), to obtain 192 mg of the title compound (yield: 47%).

Workup

  1. temperaturethe admixture was then refluxed
  2. temperaturewith heat for 20 hours
  3. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  4. dry with materialthe chloroform layer was 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-f4d927672aa4475ab91464e66cd4442f
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…