6-Methoxyquinoline → 2-Hydroxy-6-methoxyquinoline

HRID 1655024Notes

Reaction equation

HRID 1655024 reaction equation
[CH3:1][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.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:18])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 148606-MethoxyquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 2282682-Hydroxy-6-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 6-methoxyquinoline (2.08 g) in CHCl3 (45 mL) at r.t. was added m-chloroperoxybenzoic acid (3.38 g) portionwise over 10 min. After 30 min., CHCl3 (50 mL) was added and the solution washed with saturated aq. NaHCO3 (3×), dried (MgSO4) and concentrated. A portion of this material (500 mg) in DMF (10 mL) was treated with trifluoroacetic anhydride (TFAA) and stirred at r.t. for 17 hr. The TFAA was removed under vacuum and to the resulting solution was added water (60 mL). The mixture was extracted with EtOAc (6×) and the combined organics were dried (MgSO4) and concentrated. Trituration of the resulting material with acetone provided the title compound as a pale yellow solid.

Workup

  1. washthe solution washed with saturated aq. NaHCO3 (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionA portion of this material (500 mg) in DMF (10 mL) was treated with trifluoroacetic anhydride (TFAA)
  5. customThe TFAA was removed under vacuum and to the resulting solution
  6. additionwas added water (60 mL)
  7. extractionThe mixture was extracted with EtOAc (6×)
  8. dry with materialthe combined organics were dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6aaf7284e2504403800a36ef1a852eeb
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

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