Acetic Anhydride → HCID 178488021, compound

HRID 628905Notes

Reaction equation

HRID 628905 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-])=[CH:8][CH:7]=[CH:6]2.CC(OC(C)=O)=[O:16]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([OH:16])[CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2538216-Methoxyquinoline N-oxide

Product 1

HCID 178488021HCID 178488021, compoundYield 67%

Procedure

A solution of 6-methoxyquinoline 1-oxide (300 mg, 1.71 mmol) in Ac2O (5.0 mL) was refluxed for 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL), the organic layer was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated to give the crude product which was purified by silica gel column (PE/EtOAc=1/2) to give 6-methoxyquinolin-2-ol (200 mg, yield 67%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washthe organic layer was washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product which
  8. customwas purified by silica gel column (PE/EtOAc=1/2)

Sources & evidence

ORD record
ord-f3370dc3d07e4c6081d616e95bdd2e00
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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