Hydrogen Peroxide → diethyl pyridine-2,3-dicarboxylate-N-oxide

HRID 1741618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741618
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)[OH:18].OO>C(O)(=O)C>[N+:1]1([O-:18])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 108895172,3-Diethyl 2,3-pyridinedicarboxylate

Produkt 1

HCID 21847052diethyl pyridine-2,3-dicarboxylate-N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 99 g of diethyl pyridine-2,3-dicarboxylate, 7.2 mL of concentrated sulfuric acid, 85 mL of 30% hydrogen peroxide and 256 mL acetic acid is stirred and heated at 85° for 4 hours. The reaction is concentrated in vacuo, and the residue is dissolved in methylene chloride, and washed with water, then saturated sodium bicarbonate. After drying, the organic phase is concentrated in vacuo to afford 79 g of the desired product, mp 80°-85°. A portion recrystallized from carbon tetrachloride-pentane has mp 87°-88°.

Aufarbeitung

  1. temperatureheated at 85° for 4 hours
  2. concentrationThe reaction is concentrated in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washwashed with water
  5. customAfter drying
  6. concentrationthe organic phase is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0f083197b39c4f41b4d58c3f08ed1bd2
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334576

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