Sodium Hydroxide → 1-(2-Chloropyridin-4-yl)ethan-1-one

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Reaction Steps

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;

Provenance & Evidence