Water → Methyl 4-(trifluoromethyl)nicotinate

HRID 1172122

Reaktionsgleichung

Reaktionsgleichung von HRID 1172122
[C:1](=O)([O-])[O-].[K+].[K+].CI.[F:9][C:10]([F:21])([F:20])[C:11]1[C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=[CH:13][CH:12]=1.O>CN(C)C=O>[F:21][C:10]([F:9])([F:20])[C:11]1[C:16]([C:17]([O:19][CH3:1])=[O:18])=[CH:15][N:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

Produkt 1

HCID 2775680Methyl 4-(trifluoromethyl)nicotinateAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6.7 g (48.6 mmoles) of anhydrous potassium carbonate and 6.9 g (48.6 mmoles) of methyl iodide were added to a solution of 4.6 g (24.1 mmoles) of 4-trifluoromethylnicotinic acid dissolved in 70 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 12 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 2.77 g (yield: 56.1%) of methyl 4-trifluoromethylnicotinate as a yellow oily substance.

Aufarbeitung

  1. customto give rise
  2. customto a reaction
  3. customAfter confirmation of the completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Quellen und Nachweise

ORD-Eintrag
ord-c34d097382a1481a9be250c51b2aaae4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833939B2

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