Reaction #2248

Reaction equation

4-acetyl-pyridine N-oxide

phosphorus oxychloride

sodium hydroxide

→

4-acetyl-2-chloro-pyridine

Solvents

toluene

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   workup.ADDITIONtreated with Tonsil (Fluka; bentonite--colloidal aqueous aluminium silicate)
3. 3
   ConcentrationConcentration and crystallisation (diethyl ether/n-hexane)

Procedure

5.0 g (36.5 mmol) of 4-acetyl-pyridine N-oxide and 6.64 ml (73 mmol) of phosphorus oxychloride are stirred in 50 ml of toluene for 2 h at 100°. The reaction mixture is stirred at 50° into 500 ml of 10N sodium hydroxide solution, extracted with ethyl acetate and treated with Tonsil (Fluka; bentonite--colloidal aqueous aluminium silicate). Concentration and crystallisation (diethyl ether/n-hexane) give 4-acetyl-2-chloro-pyridine;

Source