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

HRID 1368176Notes

Reaction equation

HRID 1368176 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

This example illustrates the preparation of exo-3-(5,6-dichloropyrid-3-yl)-endo-3-cyano-8-methyl-8-azabicyclo[3.2.1]octane. 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-9a54568b551445fbb079c017455ae441
Source dataset
uspto-grants-2003_06
Patent number
US06573275B1

Reaction notes

Loading…