Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine hydrochloride

HRID 2200599Notes

Reaction equation

HRID 2200599 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.O=S(Cl)[Cl:12]>>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12325387(5-Methylpyridin-2-yl)methanol

Product 1

HCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideYield 91.3%

Procedure

A solution of (5-methylpyridin-2-yl)methanol in SOCl2(10 mL) was refluxed 30 min. The mixture was concentrated and dried in vacuo to give 2-(chloromethyl)-5-methylpyridine hydrochloride (2.1 g, 91.3% yield) as white solid. LCMS MH+ 142.

Workup

  1. concentrationThe mixture was concentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-c13b11f1820c4f44826724b9b69c605d
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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