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

HRID 2418246Notes

Reaction equation

HRID 2418246 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 Chloride2×HCID 10820596(4-Methoxy-pyridin-2-yl)-methanol

Product 1

HCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15 ml of thionyl chloride are added dropwise to a solution, cooled to -10° C., of 10 g (0.072 mole) of 2-hydroxymethyl-4-methoxypyridine in 30 ml of dry chloroform over the course of 15 minutes. The solution is allowed to come to room temperature and is stirred for another one and a half hours. After the solvent and the excess thionyl chloride have been stripped off, colorless crystals are obtained and are recrystallized from isopropanol to yield the title compound [12.1 g (87%), m.p. 140° to 141° C., decomposition).

Workup

  1. customto come to room temperature
  2. customcolorless crystals are obtained
  3. customare recrystallized from isopropanol

Sources & evidence

ORD record
ord-c6f03e1cbc094c4284694f2f8b8c31d9
Source dataset
uspto-grants-1984_09
Patent number
US04472409

Reaction notes

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