Hydrogen Peroxide → HCID 12498473, compound

HRID 985511Notes

Reaction equation

HRID 985511 reaction equation
[OH2:1].[N:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].OO>C(O)(=O)C.O>[N+:2]1([O-:1])[C:3]([C:11]([OH:13])=[O:12])=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 162198812,4-Pyridinedicarboxylic acid monohydrate

Product 1

HCID 12498473HCID 12498473, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A suspension of 2,4-pyridinedicarboxylic acid monohydrate (92.6 g, 0.5 mol) in acetic acid (700 ml) was treated with hydrogen peroxide (300 ml of a 35 wt % solution in water) and then heated at reflux for 16 h. The mixture was allowed to cool to 80° C., water (200 ml) was added and the mixture refrigerated at 4° C. for 16 h. The resulting solid was collected by filtration, washed with cold water (3×100 ml) and dried to give 2,4-pyridinedicarboxylic acid N-oxide (91.5 g, 91%) as a white crystalline solid. 1H NMR (360 MHz, d6-DMSO) δH 8.17 (1H, dd, J 3 and 7), 8.51 (1H, d, J 3), 8.76 (1H, d, J 7).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 16 h
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with cold water (3×100 ml)
  5. customdried

Sources & evidence

ORD record
ord-ff73419405234a4b92299c94369d70e5
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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