Acetic Anhydride → HCID 178488021, compound

HRID 1410610Notes

Reaction equation

HRID 1410610 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-e249b47d695a4947810f9066b2215bf3
Source dataset
uspto-grants-2014_12
Patent number
US08921562B2

Reaction notes

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