4-Chloro-6,7-dimethoxyquinoline → HCID 22132766, compound

HRID 1857211Notes

Reaction equation

HRID 1857211 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1.C(Cl)(Cl)Cl.CO>COCCOCCOC>[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 12299666HCID 12299666, compoundHCID 21584188Chloroform methanol

Product 1

HCID 22132766HCID 22132766, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
160 °C

Procedure

Under argon, 4-cyclohexylcarbonyl-1-hydroxybenzene (273 mg) obtained in Example 142 and 4-chloro-6,7-dimethoxyquinoline (100 mg) were dissolved in diethylene glycol dimethyl ether (0.2 ml), and the solution was refluxed at 160° C. for 30 minutes. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was washed with brine and 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/acetone and then with chloroform/methanol to obtain 58 mg of the title compound (yield: 33%).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  2. washthe chloroform layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customAfter removing the solvent
  5. distillationby reduced-pressure distillation
  6. customthe resulting residue was purified by chromatography on silica gel eluting with hexane/acetone

Sources & evidence

ORD record
ord-dac9b0bb37bc4721b0b0270719c4f018
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…