Phosphorus oxychloride → 6-Chloronicotinoyl Chloride

HRID 1702614Notes

Reaction equation

HRID 1702614 reaction equation
P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:7].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][N:14]=1>>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([Cl:7])=[O:18])=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 792226-Chloronicotinic acid

Product 1

HCID 27821656-Chloronicotinoyl Chloride

Procedure

75 Ml. of phosphorous oxychloride and 144 g. of phosphorous pentachloride were added to 100 g. of 6-chloronicotinic acid and intimately mixed. The reaction mixture was slowly heated in an oil bath to 80° over 25 minutes with stirring. The bath temperature was raised to 125° and the solution was stirred and refluxed for 1 hour. After concentration under reduced pressure, anhydrous toluene was added and the solution was concentrated again, finally on the oil pump, to yield 6-chloronicotinoyl chloride as a colorless solid.

Workup

  1. temperatureThe reaction mixture was slowly heated in an oil bath to 80° over 25 minutes
  2. temperatureThe bath temperature was raised to 125°
  3. stirringthe solution was stirred
  4. temperaturerefluxed for 1 hour
  5. concentrationAfter concentration under reduced pressure, anhydrous toluene
  6. additionwas added
  7. concentrationthe solution was concentrated again, finally on the oil pump

Sources & evidence

ORD record
ord-746a8e866c8a40a2a3d420f07401310c
Source dataset
uspto-grants-1982_09
Patent number
US04348396

Reaction notes

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