Pyridine, 2,4,6-trichloro- → 2,6-Dichloro-4-methoxypyridine

HRID 1360673Notes

Reaction equation

HRID 1360673 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.C[O-].[Na+].[C:13](OCC)(=[O:15])C.O>CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:15][CH3:13])[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

5

Reactant 3

HCID 27665Pyridine, 2,4,6-trichloro-HCID 10942334Sodium MethoxideHCID 22728543Water ethylacetate

Product 1

HCID 33199932,6-Dichloro-4-methoxypyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4,6-trichloropyridine (4.5 g) in methanol was added sodium methoxide (25% in methanol, 6.8 mL) at room temperature. The mixture was stirred for 12 h then poured into ethyl acetate/water and separated. The organic layer was washed with water, brine and dried over magnesium sulfate. Upon evaporating, the residue was purified by crystallization (100% hexanes) to give title compound as solid (3.1 g).

Workup

  1. customseparated
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customUpon evaporating
  5. customthe residue was purified by crystallization (100% hexanes)

Sources & evidence

ORD record
ord-f5b3f16c56ba46f48aa34f6b160730c0
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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