Phosphorus oxychloride → 4-Chloro-3-nitropyridine

HRID 1986343Notes

Reaction equation

HRID 1986343 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[Cl:13][C:9]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526806HCID 178526806, compound

Product 1

HCID 27357814-Chloro-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-nitro-4-pyridinol (20 g, 143 mmol) in toluene (300 mL) was added phosphorous oxychloride (65.7 g, 429 mmol) at 0° C. The resulting mixture was warmed to room temperature, then heated to reflux (110° C.) for 16 hours. After cooling to rt, the solvent was removed in vacuo and the residue was poured on ice, then basified with K2CO3 to pH≈10. The mixture was extracted with ethyl acetate and the organic phase was washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing (22.5 g, 99%). MS (ES+) m/e 159 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux (110° C.) for 16 hours
  3. temperatureAfter cooling to rt
  4. customthe solvent was removed in vacuo
  5. additionthe residue was poured on ice
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe organic phase was washed twice with water
  8. concentrationbefore concentrating to a brown oil which

Sources & evidence

ORD record
ord-bc56da32eda64438af1dadb60936d75f
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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