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

HRID 2380232Notes

Reaction equation

HRID 2380232 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 crashed 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. customformed
  5. extractionThe product was extracted with methylene chloride
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated to a brown oil, which
  8. washwas washed with hot hexane
  9. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-e549c299e3164c61982e646587b08c85
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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