Thionyl Chloride → 6-Chloronicotinoyl Chloride

HRID 1763485Notes

Reaction equation

HRID 1763485 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acid

Product 1

HCID 27821656-Chloronicotinoyl Chloride

Procedure

6-Chloronicotinic acid (67 g) was treated with thionyl chloride (130 ml) and the resulting mixture heated under reflux for 2 hours. After evaporation to dryness, 60°-80° petroleum ether (60 ml) was added, and the solution again evaporated to dryness. The resulting residue was taken up in petroleum ether (60°-80°) and the solution filtered. Partial evaporation of the filtrate, followed by cooling, gave the desired product, 6-chloronicotinoyl chloride, as a white precipitate, m.p. 45°-47° (73). The product was characterized by infra-red spectroscopy, and was used directly in the next stage without further purification.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation to dryness, 60°-80° petroleum ether (60 ml)
  4. additionwas added
  5. customthe solution again evaporated to dryness
  6. customwas taken up in petroleum ether (60°-80°)
  7. filtrationthe solution filtered
  8. customPartial evaporation of the filtrate
  9. temperatureby cooling

Sources & evidence

ORD record
ord-f45f22221e054d80acbfbc07b5837de8
Source dataset
uspto-grants-1978_09
Patent number
US04112102

Reaction notes

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