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

HRID 1936726Notes

Reaction equation

HRID 1936726 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-6f063daf26934e78a133a48543c83540
Source dataset
uspto-grants-2002_05
Patent number
US06391883B1

Reaction notes

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