4-Chloro-6,7-dimethoxyquinoline → Methyl 10-[2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methyl-phenyl]-10-oxo-decanoate

HRID 228690Notes

Reaction equation

HRID 228690 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:35][O:34][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:36][CH3:37])[N:27]=[CH:26][CH:25]=[C:24]2[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078275Methyl 10-(2-hydroxy-5-methyl-phenyl)-10-oxo-decanoate

Product 1

HCID 23078320Methyl 10-[2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methyl-phenyl]-10-oxo-decanoateYield 10.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

Methyl 10-(2-hydroxy-5-methyl-phenyl)-10-oxo-decanoate (546 mg), 4-chloro-6,7-dimethoxyquinoline (397 mg), and 4-dimethylaminopyridine (434 mg) were suspended in o-dichlorobenzene (20 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, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give methyl 10-[2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methyl-phenyl]-10-oxo-decanoate (90 mg, yield 1.0%).

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 by distillation under the reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ae8095ebc68b4b53bf9098742b29753e
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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