N,N-Dimethylaniline → 1-(5,6-Dichloropyridin-3-yl)ethan-1-one

HRID 981324Notes

Reaction equation

HRID 981324 reaction equation
O[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O.CN(C)C1C=CC=CC=1>ClC1C=CC=CC=1>[Cl:14][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178467206HCID 178467206, compound

Product 1

HCID 101980061-(5,6-Dichloropyridin-3-yl)ethan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

3.4 g (20 mmol) of 2-hydroxy-3-chloro-5-acetylpyridine are stirred with 3.7 g (24 mmol) of phosphorus oxychloride and 2.4 g (20 mmol) of N,N-dimethylaniline in 75 ml of chlorobenzene at 100° C. for 1.5 hours. The mixture is stirred into 200 ml of ice-water and extracted with ethyl acetate. Drying and evaporation gives 3.6 g (95%) of 2,3-dichloro-5-acetylpyridine, melting point: 80° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customDrying
  3. customevaporation

Sources & evidence

ORD record
ord-ca45135ad94e48e98954d206ac24bbfa
Source dataset
uspto-grants-1991_02
Patent number
US04990620

Reaction notes

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