Phosphorus oxychloride → 2-Chloroisonicotinic acid

HRID 1110975Notes

Reaction equation

HRID 1110975 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[CH:7]=[CH:6][N+:5]([O-])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:13])=O.P(Cl)(Cl)(Cl)(Cl)Cl>O>[Cl:13][C:6]1[CH:7]=[C:2]([C:1]([OH:10])=[O:9])[CH:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 261304-Pyridinecarboxylic acid, 1-oxide

Product 1

HCID 2369852-Chloroisonicotinic acidYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

87 g of isonicotinic acid N-oxide, 350 ml of phosphorus oxychloride and 192 g of phosphorus pentachloride were mixed and refluxed for 3 hours. The reaction mixture was poured into water and left to stand overnight. The resulting precipitate was collected by filtration, and recrystallized from ethanol to give 65 g (66 %) of 2-chloro-4-pyridinecarboxylic acid.

Workup

  1. temperaturerefluxed for 3 hours
  2. waitleft
  3. filtrationThe resulting precipitate was collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-de68a7f6617c422895bd6a770e33f3d6
Source dataset
uspto-grants-1990_12
Patent number
US04977267

Reaction notes

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