2-Chloro-3-methoxypyridine → 2,3-Dimethoxypyridine

HRID 2246188Notes

Reaction equation

HRID 2246188 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CN(C)C=O>[CH3:10][O:11][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 1042522-Chloro-3-methoxypyridineHCID 10942334Sodium Methoxide

Product 1

HCID 46578092,3-DimethoxypyridineYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-chloro-3-methoxypyridine (2) (13 g, 90.6 mmol), from Step I, was stirred with 3-equivalents of sodium methoxide (14.7 g, 271.8 mmol) in dimethylformamide (100 mL) at 100° C. until completion of the reaction. The reaction mixture was then quenched with water and extracted with dichloromethane. The combined extracts were washed with water, concentrated and distilled (74° C.; 5 mm Hg) to give the product, 2,3-dimethoxypyridine (3), as a clear oil (7 g; 29% yield for two steps).

Workup

  1. customThe reaction mixture was then quenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined extracts were washed with water
  4. concentrationconcentrated
  5. distillationdistilled (74° C.; 5 mm Hg)

Sources & evidence

ORD record
ord-7fa384e2807d4d1789c437b8efa79210
Source dataset
uspto-grants-2010_03
Patent number
US07687487B2

Reaction notes

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