Thionyl Chloride → 2-(Chloromethyl)-3,4-dimethoxypyridine

HRID 2051486Notes

Reaction equation

HRID 2051486 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:11]O)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O=S(Cl)[Cl:15].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:11][Cl:15])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 107258093,4-Dimethoxy-2-pyridinemethanol

Product 1

HCID 50797222-(Chloromethyl)-3,4-dimethoxypyridineYield 162.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,4-Dimethoxy-2-hydroxymethylpyridine (0.34 g, 0.002 mol) was dissolved in CH2Cl2 (8 ml). SOCl2 (0.27 g, 0.00227 mol) in CH2Cl2 (2 ml) was added under stirring at room temperature. After 10 min the mixture was neutralized with NaHCO3 (5 ml). The phases were separated, the CH2Cl2 phase was washed with NaCl-solution, dried over Na2SO4 and evaporated giving the desired product (0.61 g, 88%).

Workup

  1. customThe phases were separated
  2. washthe CH2Cl2 phase was washed with NaCl-solution
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-2f1eb111ed2d4d56825a5e486ddde6fa
Source dataset
uspto-grants-1991_05
Patent number
US05019584

Reaction notes

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