4-Chloro-6,7-dimethoxyquinoline → HCID 57756484, compound

HRID 228706Notes

Reaction equation

HRID 228706 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[OH:11])=[O:3].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[C:5]([O:11][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][CH:14]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 10515131-(4-Chloro-2-hydroxyphenyl)ethanone

Product 1

HCID 57756484HCID 57756484, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

4-Chloro-2-hydroxyacetophenone (45 mg), 4-chloro-6,7-dimethoxyquinoline (60 mg), and 4-dimethylaminopyridine (95 mg) are suspended in o-dichlorobenzene (10 ml) to prepare a suspension which was then stirred at 120° C. overnight and then at 140° C. for 5 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (11 mg, yield 12%).

Workup

  1. customto prepare a suspension which
  2. waitat 140° C. for 5 hr
  3. temperatureThe reaction solution was cooled to room temperature
  4. customthe solvent was removed by distillation under the reduced pressure
  5. additionWater was then added to the residue
  6. extractionthe mixture was extracted with chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customthe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-5e879dc3d08141aa9de7d4a9875e3262
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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