3-Pyridinemethanol → 3-(Chloromethyl)pyridine hydrochloride

HRID 2176899Notes

Reaction equation

HRID 2176899 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11]O)[CH:6]=1>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:11][C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 24386Thionyl Chloride

Product 1

HCID 233943-(Chloromethyl)pyridine hydrochlorideYield 63.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (9.60 g, 80.6 mmol) was added dropwise to a stirred solution of (pyridin-3-yl)methanol (2.20 g, 20.1 mmol) in 30 ml of CHCl3 at 0° C. and refluxed for 4 h. The reaction mixture was concentrated under reduced pressure to afford 2.10 g (63.6%) of 3-(chloromethyl)pyridine hydrochloride as a brown solid.

Workup

  1. temperaturerefluxed for 4 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-485a1367883042708fb355ca15db40aa
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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