2,6-Dichloro-4-methylpyridine → 2-Chloro-6-methoxy-4-methylpyridine

HRID 37854Notes

Reaction equation

HRID 37854 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:10][O-:11].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:11][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 108989972,6-Dichloro-4-methylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 579067102-Chloro-6-methoxy-4-methylpyridineYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,6-dichloro-4-methyl-pyridine (250 mg, 1.5 mmol) in methanol (2 mL) was added to a solution of sodium methoxide (prepared from sodium (71 mg, 3.0 mmol) and anhydrous methanol (20 mL)) and heated at reflux for 48 h. The solvent was evaporated and the residue partitioned between water and dichloromethane. The organic layer was separated, washed with water, brine, dried over anhydrous sodium sulfate and concentrated to afford 2-chloro-6-methoxy-4-methyl-pyridine (150 mg, 61%) as a pale orange oily liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. customThe solvent was evaporated
  4. customthe residue partitioned between water and dichloromethane
  5. customThe organic layer was separated
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-603760545c4845bda28eb91c90732d62
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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