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

HRID 706648Notes

Reaction equation

HRID 706648 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C1(C)C=CC=CC=1>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 122143395-(chloromethyl)-2-methylpyridine hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

(6-Methylpyridin-3-yl)methanol (8.54 g, 69.34 mmol) was dissolved in toluene (0.5M, 125 mL). Thionyl chloride (10.12 mL, 138.7 mmol) was added dropwise, during which a white solid began to precipitate out of solution. The mixture was heated to 65° C. and stirred for 1 hour. The mixture was concentrated, shaken in ether and collected by filtration to provide 5-(chloromethyl)-2-methylpyridine hydrochloride (11.3 g, 92% yield) as a beige solid.

Workup

  1. customto precipitate out of solution
  2. concentrationThe mixture was concentrated
  3. stirringshaken in ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fc5d1ed6094c419eb96ea4dd30343a2d
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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