Ethanol → 2-(6,7-Dimethoxyquinolin-4-yloxy)-5-methoxybenzoic acid

HRID 228504Notes

Reaction equation

HRID 228504 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:17]=1[C:18]([O:20]CC)=[O:19].[OH-].[Li+].C(O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:17]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 23078318Ethyl 2-(6,7-dimethoxyquinolin-4-yloxy)-5-methoxybenzoate

Product 1

HCID 230785212-(6,7-Dimethoxyquinolin-4-yloxy)-5-methoxybenzoic acidYield 105.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-(6,7-dimethoxyquinolin-4-yloxy)-5-methoxybenzoate (143 mg) and lithium hydroxide (78 mg) were suspended in a mixed solvent composed of ethanol (10 ml) and water (1 ml), and the suspension was stirred at room temperature overnight. The solvent was then removed therefrom by distillation under the reduced pressure. Water was added to the residue, and the resultant solution was neutralized with 12N hydrochloric acid. The mixture was then extracted with chloroform. The chloroform layer was washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure to give the title compound (140 mg, yield 100%).

Workup

  1. customThe solvent was then removed
  2. distillationby distillation under the reduced pressure
  3. additionWater was added to the residue
  4. extractionThe mixture was then extracted with chloroform
  5. washThe chloroform layer was washed with water and saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure

Sources & evidence

ORD record
ord-3652b072d3e8418799d34a83a04ef576
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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