Methyl iodide → methyl 4-methylnicotinate

HRID 2265131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2265131
[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

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2291634-Methylnicotinic acid

Produkt 1

HCID 10877301methyl 4-methylnicotinateAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e12522d4a74841928da3de44b019fd13
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855294B2

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