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

HRID 1033000Notes

Reaction equation

HRID 1033000 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[C:6](=O)[NH:7][C:8]=1[CH3:9])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:15]>O>[Cl:15][C:6]1[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][C:3]([CH2:1][CH3:2])=[C:8]([CH3:9])[N:7]=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 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-ethyl-6-methyl-3-nitro-2-(1H)-pyridinone (2.38 g, 13 mmol) and phosphorus pentachloride (3.3 g, 15.6 mmol) was heated under an atmosphere of nitrogen at 140°-150° C. for 15 minutes. The resultant brown oil was then treated with water and the product extracted into chloroform. The organic extract was washed three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure (15 torr). The residue was passed through a small plug of silica gel, eluted with 2% methanol in chloroform. Collection and concentration of appropriate fractions yielded 1.5 g (57.5%) of the corresponding chloropyridine as a clear pale brown oil.

Workup

  1. temperaturewas heated under an atmosphere of nitrogen at 140°-150° C. for 15 minutes
  2. extractionthe product extracted into chloroform
  3. extractionThe organic extract
  4. washwas washed three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (15 torr)
  8. washeluted with 2% methanol in chloroform
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-826ba8ecfc274e07866f41cc914d778f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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