Thionyl Chloride → 2-(Chloromethyl)-4-methoxypyridine hydrochloride

HRID 262466Notes

Reaction equation

HRID 262466 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10820596(4-Methoxy-pyridin-2-yl)-methanol

Product 1

HCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (23 cc) was added over 25 minutes to a stirred solution of 2-hydroxymethyl-4-methoxypyridine (8.935 g) in chloroform at room temperature, and the mixture was stirred for a further 2 hours and was evaporated to dryness and the residue was triturated with ether and recrystallised from 0.9 N ethanolic hydrogen chloride/ether (7:5) to give 2-chloromethyl-4-methoxypyridine hydrochloride m.p. 142° (decomp).(12.1 g).

Workup

  1. customwas evaporated to dryness
  2. customthe residue was triturated with ether
  3. customrecrystallised from 0.9 N ethanolic hydrogen chloride/ether (7:5)

Sources & evidence

ORD record
ord-034b78759a2e4edd8510db4079c56bb3
Source dataset
uspto-grants-1979_05
Patent number
US04154838

Reaction notes

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