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

HRID 444478Notes

Reaction equation

HRID 444478 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-ac019aaeed6749c48ad0596c55d30a9f
Source dataset
uspto-grants-1981_04
Patent number
US04264608

Reaction notes

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