Phosphorus trichloride → 2-Chloro-4-nitropyridine

HRID 1910747Notes

Reaction equation

HRID 1910747 reaction equation
P(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][N+:7]=1[O-].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 844332-Chloro-4-nitropyridine 1-oxideHCID 516892Sodium Bicarbonate

Product 1

HCID 7351522-Chloro-4-nitropyridineYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Phosphorus trichloride (4.2 mL, 48.7 mmol) was added to a solution of 2-chloro-4-nitro-pyridine-1-oxide (1.70 g, 9.74 mmol) in dry chloroform (25 mL) at r.t. The reaction mixture was then heated to reflux and maintained at this temperature overnight. The reaction was cooled to r.t. then poured onto ice, basified to between pH 7-8 with saturated aq. sodium bicarbonate solution and extracted with chloroform (×2). The combined organic phase was washed with water and brine, dried over sodium sulfate and concentrated. Drying under high vacuum afforded 2-chloro-4-nitro-pyridine (1.2 g, 78%) as a solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. temperaturemaintained at this temperature overnight
  4. additionthen poured onto ice
  5. extractionextracted with chloroform (×2)
  6. washThe combined organic phase was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customDrying under high vacuum

Sources & evidence

ORD record
ord-62d82b2205c642d1afaa2e799e09ec86
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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