6-Methoxyquinoline → 6-Hydroxyquinoline

HRID 1165503Notes

Reaction equation

HRID 1165503 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.C(=O)(O)[O-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 148606-MethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 113746-HydroxyquinolineYield 85.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 2.50 g (15.7 mmol, Aldrich) of 6-methoxyquinoline in 10 ml of 48% aqueous HBr was refluxed for 24 hours. The reaction mixture was cooled, added slowly to a 150 ml stirred solution of saturated aqueous sodium bicarbonate and then extracted with two 100 ml portions of ethyl acetate. The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to give a solid. The crude material was recrystallized (EtOAc/petroleum ether) to afford 1.95 g (84%) of title compound as white crystals, m.p. 194°-195°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionadded slowly to a 150 ml
  3. extractionextracted with two 100 ml portions of ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customThe crude material was recrystallized (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-cd084d845f6946c8a0b159e2f3e0fda1
Source dataset
uspto-grants-1990_03
Patent number
US04910208

Reaction notes

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