(6-Methylpyridin-2-yl)methanol hydrochloride → 2-(Chloromethyl)-6-methylpyridine

HRID 446816

Reaction equation

HRID 446816 reaction equation
[ClH:1].[CH3:2][C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][CH:4]=1>O=S(Cl)Cl>[Cl:1][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:2])[N:8]=1

Participants

3

Reactant 1

HCID 18413908(6-Methylpyridin-2-yl)methanol hydrochloride

Product 1

HCID 765462-(Chloromethyl)-6-methylpyridineYield 70.6%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of (6-methylpyridin-2-yl)methanol hydrochloride (1.0 g, 0.008 mol) in SOCl2 (3 mL) was stirred at RT for 1 h. The reaction mixture was then concentrated in vacuo to obtain the crude product. The crude material was azeotroped with toluene and the resulting residue was filtered and dried in vacuo to afford 2-(chloromethyl)-6-methylpyridine (800 mg, 63%) as a light brown solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto obtain the crude product
  3. customThe crude material was azeotroped with toluene
  4. filtrationthe resulting residue was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d56dcbc7c9984717852394e78b9c4ed7
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Linked notes

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