Phosphorus oxychloride → 2-Chloroisonicotinic acid

HRID 2738

Reaction equation

HRID 2738 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([OH:15])(=[O:14])[C:7]1[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=1>>[Cl:3][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][N:10]=1)[C:6]([OH:15])=[O:14]

Participants

3

Reactant 2

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

Product 1

HCID 2369852-Chloroisonicotinic acid

Conditions

Temperature
120 °C

Procedure

Phosphorus oxychloride (220.7 g) was added to isonicotinic acid N-oxide (50.064 g), and the mixture was stirred on an oil bath at 120° C. for 7 hours. The reaction mixture was slowly poured into ice water with vigorously stirring to precipitate light yellow crystals. The mixture was adjusted to approximately pH 4 with 4N NaOH aqueous solution. The resulting crystals were filtered out, washed with water, and dried by vacuum heating (60° C.) to obtain the above-captioned compound ([9]-(92)-467) (37.845 g).

Workup

  1. stirringwith vigorously stirring
  2. customto precipitate light yellow crystals
  3. filtrationThe resulting crystals were filtered out
  4. washwashed with water
  5. customdried by vacuum
  6. temperatureheating (60° C.)
  7. customto obtain the above-captioned compound ([9]-(92)-467) (37.845 g)

Sources & evidence

ORD record
ord-8debf37587f1426b9a2fd8782e5c9316
Source dataset
uspto-grants-1998_03
Patent number
US05731310

Linked notes

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