Phosphorus pentachloride → 4-Chloro-3-nitropyridine

HRID 1370193Notes

Reaction equation

HRID 1370193 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].P(Cl)(Cl)(Cl)(Cl)[Cl:12]>ClC(Cl)C>[Cl:12][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178526806HCID 178526806, compound

Product 1

HCID 27357814-Chloro-3-nitropyridineYield 76%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

5 g of 4-hydroxy-3-nitropyridine and 15.5 g of phosphorous pentachloride were added to 100 ml of dichloroethane and reacted under reflux for 90 minutes. When it was poured onto ice to separate an organic phase and allowed to stand at room temperature for a while, crystals were precipitated. They were collected by filtration and washed with hexane, to give 4.3 g of the title compound.

Workup

  1. customreacted
  2. temperatureunder reflux for 90 minutes
  3. additionWhen it was poured onto ice
  4. customto separate an organic phase
  5. customto stand at room temperature for a while, crystals
  6. customwere precipitated
  7. filtrationThey were collected by filtration
  8. washwashed with hexane

Sources & evidence

ORD record
ord-752ce13ba4b9461b9fc2b0039feef47c
Source dataset
uspto-grants-2003_06
Patent number
US06583138B1

Reaction notes

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