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

HRID 263234Notes

Reaction equation

HRID 263234 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-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-ffc4a63aef364ac1bddee86b346a8749
Source dataset
uspto-grants-1979_05
Patent number
US04156727

Reaction notes

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