Phosphorus oxychloride → 2-Chloro-4-methyl-3-nitropyridine

HRID 53518Notes

Reaction equation

HRID 53518 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13].P(Cl)(Cl)(Cl)=O>>[Cl:13][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178428606HCID 178428606, compound

Product 1

HCID 3453632-Chloro-4-methyl-3-nitropyridine

Procedure

A mixture of 25 g of 2-hydroxy-4-methyl-3-nitropyridine, 12.5 g of phosphorous pentachloride, and 62 ml of phosphorous oxychloride was refluxed for 2 hrs. After cooling, the mixture was poured onto crushed ice and stirred until a precipitate formed. The product was extracted with methylene chloride, dried (sodium sulfate) and concentrated to a brown oil, which was washed with hot hexane. Concentration in vacuo provided 16.2 g of the the title compound, m.p. 45°-47° C.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. temperatureAfter cooling
  3. additionthe mixture was poured
  4. customonto crushed ice
  5. customformed
  6. extractionThe product was extracted with methylene chloride
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated to a brown oil, which
  9. washwas washed with hot hexane
  10. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-73144cc5669447789f248444d3d67268
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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