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

HRID 1292042Notes

Reaction equation

HRID 1292042 reaction equation
O[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.O=S(Cl)[Cl:12]>C(Cl)Cl>[Cl:12][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 302564(2-Methylpyridin-3-yl)methanol

Product 1

HCID 122437113-(Chloromethyl)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-hydroxymethyl-2-methylpyridine (1.00 g, 8.13 mmol) from step 1 above in CH2Cl2 (40 mL) at ambient temperature was added SOCl2 (9.5 g, 80 mmol). The mixture was stirred for 4 h, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated, and the aqueous layer was washed with additional CH2 Cl2 (2×40 mL). The combined organic layers were evaporated under reduced pressure to give 3-chloromethyl-2-methyl-pyridine as a solid which was used in the next step without purification (TLC: Rf = 0.85 (95:5 CH2Cl2 :MeOH); FAB MS m/z 142 (M+ +H)).

Workup

  1. customthe solvent and excess SOCl2 were evaporated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (100 mL)
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with additional CH2 Cl2 (2×40 mL)
  5. customThe combined organic layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-27235d4734b7402294690266c6f2d812
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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