Thionyl Chloride → 2-(Chloromethyl)-3-methoxypyridine hydrochloride

HRID 262454Notes

Reaction equation

HRID 262454 reaction equation
O[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[ClH:13].[Cl:13][CH2:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5324774(3-Methoxypyridin-2-yl)methanol

Product 1

HCID 204742082-(Chloromethyl)-3-methoxypyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Hydroxymethyl-3-methoxypyridine (4.2 g) was dissolved in chloroform (60 ml) and to the stirred solution was added thionyl chloride (6 ml). The mixture was stirred for 90 minutes and the solvent evaporated and the residue was recrystallised from ethanol/ether to give 2-chloromethyl-3methoxypyridine hydrochloride (5.1 g), m.p. 171.5°-172.5°.

Workup

  1. customthe solvent evaporated
  2. customthe residue was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-e87dda5a3b5d4dc9aa27dd3d364da19a
Source dataset
uspto-grants-1979_05
Patent number
US04154838

Reaction notes

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