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

HRID 1109723Notes

Reaction equation

HRID 1109723 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 74694'-HydroxyacetophenoneHCID 79732-Bromopyridine

Product 1

HCID 143993361-{4-[(Pyridin-2-yl)oxy]phenyl}ethan-1-oneYield 73%

Procedure

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%).

Workup

  1. customby Ullmann reaction

Sources & evidence

ORD record
ord-139642ec458741faa7aef75f62ea0d6e
Source dataset
uspto-grants-1994_06
Patent number
US05322845

Reaction notes

Loading…