Thionyl Chloride → 2-(Chloromethyl)-3-methylpyridine hydrochloride

HRID 911426Notes

Reaction equation

HRID 911426 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[ClH:12].[Cl:12][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1514369(3-Methylpyridin-2-yl)methanol

Product 1

HCID 130586832-(Chloromethyl)-3-methylpyridine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-hydroxymethyl-3-methylpyridine (90 mg, 0.73 mmol) in dry DCM (10 mL) at ambient temperature, add with stirring thionyl chloride (0.53 mL, 7.3 mmol). Continue stirring overnight, concentrate in vacuo, and azeotrope three times with chloroform. Triturate the residue with dry ether, filter, and dry under vacuum to obtain the title compound as a beige solid (130 mg, 100%).

Workup

  1. concentrationconcentrate in vacuo
  2. customTriturate the residue with dry ether
  3. filtrationfilter
  4. customdry under vacuum

Sources & evidence

ORD record
ord-30ea27fd04ed44f3b402b4efa8ae46c7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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