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

HRID 2041309Notes

Reaction equation

HRID 2041309 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-1a63c0b1387343ab8379635ef461622c
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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