Nitric Acid → 2-(1-Imidazolyl)-4-nitropyridine N-oxide

HRID 1838246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838246
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=2[O-:12])[CH:5]=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>O>[N:1]1([C:6]2[CH:11]=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=[CH:8][N+:7]=2[O-:12])[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 11430Potassium CarbonateHCID 691085752-(1-Imidazolyl)pyridine N-oxide

Produkt 1

HCID 667216462-(1-Imidazolyl)-4-nitropyridine N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A 3.22 g portion of 2-(1-imidazolyl)pyridine N-oxide was added to 7.6 g of concentrated sulfuric acid, a mixed solution of 5.2 g of fuming nitric acid and 2.6 g of concentrated sulfuric acid was gradually added dropwise thereto, and then the mixture was heated at 130° C. for about 2.5 hours. The reaction mixture was spontaneously cooled, poured into 150 g of ice-cooled water, neutralized with potassium carbonate and then extracted with 300 ml of ethyl acetate. The organic layer was dried and then concentrated, and the thus obtained mixture was subjected to a silica gel column chromatography and eluted with chloroform-methanol-28% aqueous ammonia (200:0.9:0.1, v/v/v) to obtain 0.12 g of the title compound as yellow crystals.

Aufarbeitung

  1. temperatureThe reaction mixture was spontaneously cooled
  2. extractionextracted with 300 ml of ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. washeluted with chloroform-methanol-28% aqueous ammonia (200:0.9:0.1, v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-5dccf03540a34d44a122a6162c72698f
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673799B1

Notizen zur Reaktion

Wird geladen…