Phosphorus oxychloride → 2-Chloronicotinic acid

HRID 1679545Notes

Reaction equation

HRID 1679545 reaction equation
O[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].P(Cl)(Cl)([Cl:13])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:13][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178418543HCID 178418543, compound

Product 1

HCID 762582-Chloronicotinic acid

Procedure

Heat a mixture consisting of 24.4 g of 2-hydroxy nicotinic acid and 42 ml. of phosphorous oxychloride to 100°-108° C and hold for 1 hour. Add 36.4 g of phosphorous pentachloride and heat the resulting mixture at reflux for another hour. Remove the excess phosphorous oxychloride in vacuo and pour the viscous residue on ice with stirring. Age the resulting slurry at room temperature for about 12 hours. The slurry is filtered, washed and dried to yield 2-chloro-nicotinic acid, m.p. 190° C.

Workup

  1. temperatureHeat a mixture
  2. temperatureheat the resulting mixture
  3. temperatureat reflux for another hour
  4. customRemove the excess phosphorous oxychloride in vacuo
  5. additionpour the viscous residue on ice
  6. filtrationThe slurry is filtered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-b4f4748dfccd444cbc0f12103725ceb9
Source dataset
uspto-grants-1978_03
Patent number
US04081451

Reaction notes

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