Nitric Acid → diethyl 5-nitropyridine-2,3-dicarboxylate-N-oxide

HRID 1898787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898787
C(OC(=O)C)(=O)C.[N+:8]1([O-:24])[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[N+:25]([O-])([OH:27])=[O:26]>C(O)(=O)C>[N+:25]([C:12]1[CH:11]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N+:8]([O-:24])[CH:13]=1)([O-:27])=[O:26]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 21847052diethyl pyridine-2,3-dicarboxylate-N-oxide

Produkt 1

HCID 15451775diethyl 5-nitropyridine-2,3-dicarboxylate-N-oxideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

255 ml of acetic anhydride were added to a mixture of 203.2 g (0.85 mol) of diethyl pyridine-2,3-dicarboxylate-N-oxide in 1.2 l of glacial acetic acid. 68.3 g (1.06 mol) of 98% strength nitric acid were then added in the course of 40 minutes at from 20° to 28° C. with gentle cooling and stirring and the mixture was stirred at 30° C. for 12 hours. The reaction solution was poured into 3.5 l of ice-water and extracted with methylene chloride. The organic phase was extracted in succession with water, saturated sodium hydrogencarbonate solution and sodium chloride solution, dried over magnesium sulfate and filtered off with suction through silica gel. After concentration, 177.6 g (78% of theory) of diethyl 5-nitropyridine-2,3-dicarboxylate-N-oxide were obtained of nD25 =1.5290. A sample crystallized after relatively long standing; m.p. 84°-86° C.

Aufarbeitung

  1. temperaturewith gentle cooling
  2. stirringthe mixture was stirred at 30° C. for 12 hours
  3. extractionextracted with methylene chloride
  4. extractionThe organic phase was extracted in succession with water, saturated sodium hydrogencarbonate solution and sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered off with suction through silica gel
  7. concentrationAfter concentration

Quellen und Nachweise

ORD-Eintrag
ord-3bd7a3db6909405e8b3f27e0df21b2a0
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05571774

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