4-Chloro-6,7-dimethoxyquinoline → Propyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-acetylbenzoate

HRID 228629Notes

Reaction equation

HRID 228629 reaction equation
[C:1]([C:4]1[CH:15]=[C:8]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[C:7]([OH:16])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].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.ClC1C=CC=CC=1Cl>[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:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:15][C:8]=1[C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10]

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078328Propyl 5-acetylsalicylate

Product 1

HCID 57756400Propyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-acetylbenzoateYield 18.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

Propyl 5-acetylsalicylate (202 mg), 4-chloro-6,7-dimethoxyquinoline (101 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. 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. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give the title compound (35 mg, yield 9%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0e0c4e37f57f459d8ebd25c4fd2d5b6f
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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