Phosphorus oxychloride → 4-Chloro-3-nitropyridine

HRID 1491633Notes

Reaction equation

HRID 1491633 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]>>[Cl:3][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526806HCID 178526806, compound

Product 1

HCID 27357814-Chloro-3-nitropyridineYield 97.8%

Procedure

Phosphorus oxychloride (25 ml, 0.27 mol) was added to 4-hydroxy-3-nitropyridine (7.0 g, 50.0 mmol), followed by reaction at 80° to 90° C. for 1.5 hours. Phosphorus oxychloride was removed by distillation. About 100 g of ice was added to the residue, and 28% aqueous ammonia was added dropwise thereto to adjust the pH to 7. Then, 100 ml of water was added thereto, and the aqueous mixture was extracted three times with 200 ml of dichloromethane. The resulting dichloromethane layer was dried, and then dichloromethane was removed by distillation under reduced pressure to obtain 7.75 g of a yellow liquid (yield: 97.8%).

Workup

  1. customfollowed by reaction at 80° to 90° C. for 1.5 hours
  2. customPhosphorus oxychloride was removed by distillation
  3. additionAbout 100 g of ice was added to the residue, and 28% aqueous ammonia
  4. additionwas added dropwise
  5. additionThen, 100 ml of water was added
  6. extractionthe aqueous mixture was extracted three times with 200 ml of dichloromethane
  7. dry with materialThe resulting dichloromethane layer was dried
  8. customdichloromethane was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1867eabfa4ea4aefa67eb156a22d0ff2
Source dataset
uspto-grants-1994_12
Patent number
US05371086

Reaction notes

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