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

HRID 2083042Notes

Reaction equation

HRID 2083042 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 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-3-methoxypyridine 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-925cff30090c483fa56b995d50c32d84
Source dataset
uspto-grants-1978_04
Patent number
US04083983

Reaction notes

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