Phosphorus oxychloride → 2-Chloroisonicotinic acid

HRID 1635515Notes

Reaction equation

HRID 1635515 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>>[Cl:13][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=1)[C:1]([OH:10])=[O:9]

Participants

3

Reactant 2

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

Product 1

HCID 2369852-Chloroisonicotinic acidYield 65.4%

Procedure

A mixture of isonicotinic acid N-oxide (28.0 g, 0.2 mol) and phosphorus oxychloride (120.0 g, 0.8 mol) was heated at reflux for 7 h. The reaction mixture was cooled and carefully poured into 600 mL of ice water. The precipitate was collected by filtration to give 20.6 g (65% yield) of product as a pale yellow solid, mp: 248-249 C (lit: 250-252 C).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2e5b0fb551f247d597ad11fd2fae6da2
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

Loading…