Phosphorus pentachloride → 2-Chloro-5-ethyl-6-methyl-3-nitropyridine

HRID 1033004Notes

Reaction equation

HRID 1033004 reaction equation
[N+:1]([C:4]1[C:5](=O)[NH:6][C:7]([CH3:12])=[C:8]([CH2:10][CH3:11])[CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:15]>C(Cl)(Cl)Cl>[Cl:15][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([CH2:10][CH3:11])=[C:7]([CH3:12])[N:6]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 103523142(1H)-Pyridinone, 5-ethyl-6-methyl-3-nitro-

Product 1

HCID 103755472-Chloro-5-ethyl-6-methyl-3-nitropyridineYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-nitro-5-ethyl-6-methylpyridin-2(1H)-one (0.91 g, 5.0 mmol) and phosphorus pentachloride (1.25 g, 6.0 mmol), under a nitrogen atmosphere, was heated at 140° C. for 0.5 hours. The cooled mixture was diluted with chloroform and ice water. The separated chloroform layer was then washed with water, saturated aqueous NaHCO3 and dried (Na2SO4). After filtering through a pad of charcoal, solvent was evaporated to yield 672 mg (67%) of product.

Workup

  1. washThe separated chloroform layer was then washed with water, saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationAfter filtering through a pad of charcoal, solvent
  4. customwas evaporated

Sources & evidence

ORD record
ord-3861344d06fa41ed90f224e026380e4b
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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