Phosphorus pentachloride → 4-Chloro-3-nitropyridine

HRID 1192303Notes

Reaction equation

HRID 1192303 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]>O=P(Cl)(Cl)Cl>[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 117.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To a solution of 4-hydroxy-3-nitro-pyridine (2 g, 14 mmol) in POCl3 (6 mL) was added PCl5 (2.5 g, 12 mmol). The mixture was heated to reflux for 3 hours. The solvent was evaporated and the residue was cooled with ice-water and vigorously stirred with water (3 mL) and CHCl3 (6 mL). The aqueous was extracted CHCl3 (5×5 mL). The organic phase was combined and dried over MgSO4. After filtration, the solvent was removed to afford the product 4-Chloro-3-nitro-pyridine (2.24 g, 99%). 1H NMR (CDCl3, 400 Hz) δ 9.13 (s, 1H), 8.70 (d, J=5.2 Hz, 1H), 7.55 (d, J=5.6 Hz, 1H). MS (ESI+) [M+H]+ 159.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was evaporated
  4. temperaturethe residue was cooled with ice-water
  5. extractionThe aqueous was extracted CHCl3 (5×5 mL)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-044ca69f6d5f43c295623d21f09748c2
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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