Methyl iodide → Ethyl 2-methoxyisonicotinate

HRID 1737570Notes

Reaction equation

HRID 1737570 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH3:13]I>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+].[Ag+]>[CH3:13][O:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178469239HCID 178469239, compound

Product 1

HCID 13681280Ethyl 2-methoxyisonicotinateYield 86%

Reagents, catalysts & solvents 2

HCID 92796Silver carbonateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-hydroxy-pyridine-4-carboxylate (1.0 g, 6 mmol), (Chem. Abs. 1957, 8740c), methyl iodide (1 ml) and silver(I)carbonate (1.64 g) in toluene (20 ml) was heated at reflux for 2 hours. The mixture was allowed to cool and the insolubles removed by filtration through diatomaceous earth and the pad was washed through with ethyl acetate. The filtrate was washed with water, dried (MgSO4) and the solvent removed by evaporation to give ethyl 2-methoxy-pyridine-4-carboxylate (0.93 g, 86%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customthe insolubles removed by filtration through diatomaceous earth
  5. washthe pad was washed through with ethyl acetate
  6. washThe filtrate was washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-a986088963044d95ada1cc7f125f87f2
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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