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

Participants

Reaction Steps

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.

Provenance & Evidence