6-(Benzyloxy)-4-chloro-7-methoxyquinoline → 6-Hydroxy-7-methoxyquinoline

HRID 228870Notes

Reaction equation

HRID 228870 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2Cl)C1C=CC=CC=1>C(N(CC)CC)C.CN(C)C=O.[OH-].[Pd+2].[OH-]>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[CH:12]2

Participants

4

Reactant 1

HCID 230227816-(Benzyloxy)-4-chloro-7-methoxyquinoline

Product 1

HCID 230784296-Hydroxy-7-methoxyquinolineYield 84.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 22056947triethylamine N,N-dimethylformamideSolvent

Procedure

6-Benzyloxy-4-chloro-7-methoxy-quinoline (525 mg) was dissolved in triethylamine/N,N-dimethylformamide (5 ml/20 ml) to prepare a solution. 20% palladium hydroxide (1.52 g) was added to the solution, and the mixture was stirred at room temperature under a hydrogen gas atmosphere for 6 hr. The reaction solution was filtered, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, the mixture was extracted with chloroform, and the chloroform layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 6-hydroxy-7-methoxyquinoline (258 mg, yield 84%).

Workup

  1. customto prepare a solution
  2. filtrationThe reaction solution was filtered
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washthe chloroform layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-eb59b987039f4a0c90b72e51d382aaad
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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