Phosphorus oxychloride → 2,3-Dichloro-5-nitropyridine

HRID 582028Notes

Reaction equation

HRID 582028 reaction equation
[Cl:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.P(Cl)(Cl)([Cl:14])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:14][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178526838HCID 178526838, compound

Product 1

HCID 27631062,3-Dichloro-5-nitropyridine

Procedure

3-Chloro-2-hydroxy-5-nitropyridine (4.8 g) was added to phosphorus oxychloride (11 ml) and phosphorus pentachloride (4.45 g) and the mixture refluxed overnight. The mixture was then cooled to room temperature and evaporated under reduced pressure. Iced water was added to the mixture and a solid product formed. The solid was removed by filtration, washed with water and air-dried to give 2,3-dichloro-5-nitropyridine (3.94 g).

Workup

  1. temperaturethe mixture refluxed overnight
  2. customevaporated under reduced pressure
  3. additionIced water was added to the mixture
  4. customa solid product formed
  5. customThe solid was removed by filtration
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-0eb51e2555c2420d950634206eeb0caa
Source dataset
uspto-grants-1999_07
Patent number
US05922732

Reaction notes

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