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

HRID 1741618Notes

Reaction equation

HRID 1741618 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-0f083197b39c4f41b4d58c3f08ed1bd2
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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