Water → 5-Nitropicolinic acid

HRID 374417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 374417
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10](C(OCC)=O)C(OCC)=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH-:21].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:29]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:29])=[O:21])=[N:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 516875Potassium Permanganate2×HCID 2794558Diethyl 2-(5-nitropyridin-2-yl)malonate

Produkt 1

HCID 5204885-Nitropicolinic acid

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Diethyl 2-(5-nitropyridin-2-yl)malonate (67.47 g) was stirred in water and aqueous sodium hydroxide solution (2N) was added followed by potassium permanganate (42 g) causing the reaction temperature to rise to 60° C. Further portions of aqueous sodium hydroxide solution and potassium permanganate were added maintaining the reaction temperature at 60°-70° C. After the final addition, the suspension was stirred at 60° C. for 1.5 hours. The hot suspension was then filtered through `Hyflo Supercel`. The filter cake was washed with aqueous sodium hydroxide solution (2N). On cooling to room temperature, the filtrate was carefully acidified to pH 1-2 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration and dried to yield 5-nitropyridine-2-carboxylic acid (26.17 g) as a fawn solid, m.p. 210°-211° C.

Aufarbeitung

  1. customto rise to 60° C
  2. temperaturemaintaining the reaction temperature at 60°-70° C
  3. additionAfter the final addition
  4. filtrationThe hot suspension was then filtered through `Hyflo Supercel`
  5. washThe filter cake was washed with aqueous sodium hydroxide solution (2N)
  6. temperatureOn cooling to room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d30c23b8206947fb9e3bfde8907309fa
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05480857

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