4-Chloro-3-methoxy-2-methylpyridine → 3,4-Dimethoxy-2-methylpyridine

HRID 649210Notes

Reaction equation

HRID 649210 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[CH3:11][O-:12].[Na+]>CO>[CH3:10][O:9][C:3]1[C:4]([CH3:8])=[N:5][CH:6]=[CH:7][C:2]=1[O:12][CH3:11]

Participants

4

Reactant 2

HCID 105830464-Chloro-3-methoxy-2-methylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 6398793,4-Dimethoxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-chloro-3-methoxy-2-methylpyridine (3.2 g) in methanol (5 ml) was added dropwise under ice-cooling a solution of 28% sodium methylate in methanol (20 ml) and the mixture, refluxed for 10 hours, and concentrated to dryness. To the residue, were added ice-water (10 ml) and then chloroform (100 ml) in this order, and the chloroform layer was separated, washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, to give 3,4-dimethoxy-2-methylpyridine (2.95 g) as a light brown oil.

Workup

  1. temperaturethe mixture, refluxed for 10 hours
  2. concentrationconcentrated to dryness
  3. additionTo the residue, were added ice-water (10 ml)
  4. customchloroform (100 ml) in this order, and the chloroform layer was separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-85ee90f0b41549cb94906eaf1651fe9d
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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