Sodium Hydroxide → 7-Methylquinolin-6-ol

HRID 228868

Reaction equation

HRID 228868 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]=[CH:8][CH:7]=[CH:6]2.[OH-].[Na+].C(=O)([O-])O.[Na+]>Br(O)(=O)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 155348986-Methoxy-7-methylquinoline

Product 1

HCID 128389567-Methylquinolin-6-olYield 47.2%

Reagents, catalysts & solvents 1

HCID 24445Bromic acidSolvent

Procedure

6-Methoxy-7-methyl-quinoline (3 g) was added to an aqueous bromic acid solution (30 ml), and the mixture was heated under reflux for 7 hr. The reaction solution was cooled to room temperature, the aqueous layer was then neutralized with an aqueous sodium hydroxide solution and an aqueous sodium hydrogencarbonate solution. The organic layer was extracted with ether, the solvent was removed by distillation under the reduced pressure, and the residue was washed with cooled ether to give 6-hydroxy-7-methylquinoline (1.3 g, yield 47%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. extractionThe organic layer was extracted with ether
  4. customthe solvent was removed by distillation under the reduced pressure
  5. washthe residue was washed with cooled ether

Sources & evidence

ORD record
ord-a88db85475c740678b93231be4afa665
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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