Sodium Hydroxide → 4-Methoxy-5-methoxycarbonyl-nicotinic acid

HRID 1442899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442899
C[O:2][C:3](=[O:16])[C:4]1[C:9]([O:10][CH3:11])=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=[N:6][CH:5]=1.[OH-].[Na+]>CO.O>[CH3:11][O:10][C:9]1[C:4]([C:3]([OH:16])=[O:2])=[CH:5][N:6]=[CH:7][C:8]=1[C:12]([O:14][CH3:15])=[O:13]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22019197Methyl-4-methoxy-5-methoxycarbonyl-nicotinate

Produkt 1

HCID 220191954-Methoxy-5-methoxycarbonyl-nicotinic acidAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 5.3 g (23.5 mmol) of methyl-4-methoxy-5-methoxycarbonyl-nicotinate in 150 ml of methanol and 50 ml of water is added a solution of 0.94 g (23.5 mmol) of sodium hydroxide in 10 ml of water. The resulting mixture is stirred at room temperature overnight. The methanol is removed under vacuum, the aqueous solution is made slightly acidic and extracted with ethyl acetate. The combined organic phases are dried and filtered through silica. The filtrate is evaporated to near dryness and diluted with diisopropyl ether. A precipitate is obtained, filtered off and dried. There is obtained 2.83 g (57% yield) of a white solid (M+1=212).

Aufarbeitung

  1. customThe methanol is removed under vacuum
  2. extractionextracted with ethyl acetate
  3. customThe combined organic phases are dried
  4. filtrationfiltered through silica
  5. customThe filtrate is evaporated
  6. additiondiluted with diisopropyl ether
  7. customA precipitate is obtained
  8. filtrationfiltered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d6079ad4ea5a4e8b956905e2fb6591a3
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659307B2

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