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

HRID 2152

Reaction equation

HRID 2152 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:13])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([Cl:13])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 3375424-Acetylpyridine-N-oxide

Product 1

HCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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;

Workup

  1. extractionextracted with ethyl acetate
  2. additiontreated with Tonsil (Fluka; bentonite--colloidal aqueous aluminium silicate)
  3. concentrationConcentration and crystallisation (diethyl ether/n-hexane)

Sources & evidence

ORD record
ord-6eee014e31484dc4a5b6680a1edc957c
Source dataset
uspto-grants-1998_03
Patent number
US05728708

Linked notes

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