O-Xylene → HCID 22132737, compound

HRID 1857194Notes

Reaction equation

HRID 1857194 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.Cl[C:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:38][O:37][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][C:33]=1[O:39][CH3:40])[N:30]=[CH:29][CH:28]=[C:27]2[O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 112298054-(4-hydroxybenzoyl)benzonitrile

Product 1

HCID 22132737HCID 22132737, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under argon, 4-(4-hydroxybenzoyl)benzonitrile (230 mg) obtained in Example 123 and 4-dimethylaminopyridine (138 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (230 mg) was added, and the admixture was refluxed with heat for 20 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 by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1) to obtain 199 mg of the title compound (yield: 47%).

Workup

  1. temperaturethe admixture was 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 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-3caba43c70c54748946cdecd28000861
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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