Acetic Anhydride → 4-[(3-Chlorophenyl)methoxy]-2(1H)-pyridinone

HRID 2202952Notes

Reaction equation

HRID 2202952 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=1.C(OC(=O)C)(=[O:19])C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][NH:10][C:9](=[O:19])[CH:8]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 121386214HCID 121386214, compound

Product 1

HCID 896905544-[(3-Chlorophenyl)methoxy]-2(1H)-pyridinone

Procedure

To 4-((3-chlorobenzyl)oxy)pyridine 1-oxide (2.0 g) was added acetic anhydride (20 ml), and the solution was heated at reflux for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was diluted with MeOH/NaOH (1:1, 150 ml) and heated at reflux for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with water and extracted with DCM. The combined DCM layer was concentrated in vacuo and the crude residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (984 mg) as an off-white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 4 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with MeOH/NaOH (1:1, 150 ml)
  5. temperatureheated
  6. temperatureat reflux for 1 h
  7. temperatureThe reaction mixture was cooled to room temperature
  8. concentrationconcentrated in vacuo
  9. additionThe residue was diluted with water
  10. extractionextracted with DCM
  11. concentrationThe combined DCM layer was concentrated in vacuo
  12. customthe crude residue was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-41c8046c5a9d46fb871767ccd3b480e0
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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