Methyl iodide → methyl 4-methylnicotinate

HRID 2265131Notes

Reaction equation

HRID 2265131 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH3:9][C:10]1[C:15]([C:16]([OH:18])=[O:17])=[CH:14][N:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH3:9][C:10]1[C:15]([C:16]([O:18][CH3:1])=[O:17])=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2291634-Methylnicotinic acid

Product 1

HCID 10877301methyl 4-methylnicotinateYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, 6.89 g of potassium carbonate and 4.6 mL of methyl iodide were added in that order to N,N-dimethylformamide (100 mL) solution of 6.86 g of 4-methylnicotinic acid, and stirred at room temperature for 3 hours. The solvent was evaporated off under reduced pressure, then aqueous sodium hydrogencarbonate solution was added to the residue and extracted with chloroform. The chloroform layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=50/50) to obtain 2.52 g of the entitled compound as a yellow oily substance.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. additionaqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated off under reduced pressure
  7. customthe residue was separated
  8. custompurified through silica gel column chromatography (hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-e12522d4a74841928da3de44b019fd13
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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