Methyl iodide → Ethyl 2-methoxyisonicotinate

HRID 1384621Notes

Reaction equation

HRID 1384621 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. 1H NMR Spectrum: (CDCl3) 1.30(t, 3H); 3.90(s, 3H); 4.30(q, 2H); 7.24(s, 1H); 7.35(d, 1H); 8.20(d, 1H) MS-ESI: 182 [MH]+

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-6719426b170d4a838acfc935c98a611b
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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