Water → 6,7-Dimethoxy-4-[(6-methoxy-3-pyridinyl)oxy]quinoline

HRID 228741Notes

Reaction equation

HRID 228741 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:23][O-:24].[Na+].O>C1(C)C=CC=CC=1>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH3:22])[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:5]1[CH:6]=[N:7][C:2]([O:24][CH3:23])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 230784034-[(6-Chloropyridin-3-yl)oxy]-6,7-dimethoxyquinoline2×

Product 1

HCID 230785336,7-Dimethoxy-4-[(6-methoxy-3-pyridinyl)oxy]quinolineYield 61.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(6-Chloro-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 206) (145 mg) and sodium methoxide (87 mg) were suspended in toluene (1.2 ml), and the suspension was heated under reflux for 20 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. 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 (88 mg, yield 61%).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 20 hr
  3. extractionthe mixture was extracted with chloroform
  4. washThe chloroform layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-feee1c613adc4d2fa064a8233f15e1c6
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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