4'-Hydroxyacetophenone → 1-{4-[(Pyridin-2-yl)oxy]phenyl}ethan-1-one

Participants

Reaction Steps

4'-Hydroxyacetophenone was condensed with 2-bromopyridine by Ullmann reaction to obtain 4'-(pyridine-2-yloxy)acetophenone (yield 73%). This was converted to Mannich base with dimethylamine hydrochloride and paraformaldehyde (yield 56%), which was then cyclized by reacting with 1-ethoxycarbonylmethylpyridinium chloride and ammonium acetate in N,N-dimethyl formamide, (as described in Synthesis (1976), pages 1-24) to obtain 6-[4-(pyridine-2-yloxy)phenyl]-2-pyridone (yield 32%).

Provenance & Evidence