Chloroform → 2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride

HRID 1379087Notes

Reaction equation

HRID 1379087 reaction equation
OC[C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([CH3:12])=[CH:5][N:4]=1.[CH:13]([Cl:16])(Cl)[Cl:14]>>[ClH:14].[Cl:16][CH2:13][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([CH3:12])=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 6212ChloroformHCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

Product 1

HCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideYield 69%

Procedure

To a solution of crude 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine (23.41 g, 0.41 mol) in CHCl3 (70 ml) was added SO2Cl2 (30 ml, 0.42 mol) at ice bath temperature. The reaction mixture was refluxed for 2 h and cooled to rt. Evaporation of the solvent in vacuo gave a dark brown solid. Recrystallization from isopropanol-ether gave 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride (14) (21.6 g, 69%) as a white solid; mp 135-136° C. For previous syntheses see references cited in Brandstrom et al., Acta Chemica Scandinavia 43: 536-548, 1989 and GB 2134523.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customEvaporation of the solvent in vacuo
  3. customgave a dark brown solid
  4. customRecrystallization from isopropanol-ether

Sources & evidence

ORD record
ord-0198fff3c44b4f0c8fc972b14149e244
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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