Thionyl Chloride → 2-Chloro-3-chloromethyl-pyridine

HRID 249491Notes

Reaction equation

HRID 249491 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=O.S(Cl)([Cl:13])=O>ClCCCl>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][Cl:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 115283992-Chloro-3-chloromethyl-pyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 10.24 g (0.065 mole) of 2-chloronicotinic acid were added 20 ml of 1,2-dichloroethane and 9.5 ml of thionyl chloride and the mixture was refluxed for 1 hour. The reaction mixture was concentrated to give 11.9 g of 2-chloronicotinyl chloride as an orange-colored oil. When left standing at room temperature, this product solidified thoroughly.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-474504c28abe4a759977d2ac2ba12c3e
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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