Hydrogen Peroxide → 5-Methoxycarbonylpyridine-2-carboxylic acid 1-oxide

HRID 2258307Notes

Reaction equation

HRID 2258307 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[CH:4]=[CH:3][C:2]=1[C:11]([O:13]C)=[O:12].[OH:15]O>C(O)(=O)C>[CH3:10][O:9][C:7]([C:5]1[CH:6]=[N+:1]([O-:15])[C:2]([C:11]([OH:13])=[O:12])=[CH:3][CH:4]=1)=[O:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 234911Dimethyl 2,5-pyridine dicarboxylate

Product 1

HCID 199603735-Methoxycarbonylpyridine-2-carboxylic acid 1-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

12 g (60 mmol) of dimethyl pyridine-2,5-dicarboxylate were suspended in 30 ml of glacial acetic acid, and after that 13 ml of hydrogen peroxide (35%) were added at and while stirring. The mixture was then heated to 100° C. (internal temperature), while stirring, with a clear solution being formed at 50° C. After the mixture had been stirred at 100° C. for 90 minutes, it was allowed to cool down to 20° C. and the crystalline precipitate was filtered off with suction and washed with water; after drying, 7.5 g of product were obtained, m.p. 160° C. (decomp.).

Workup

  1. stirringwhile stirring, with a clear solution
  2. custombeing formed at 50° C
  3. stirringAfter the mixture had been stirred at 100° C. for 90 minutes
  4. temperatureto cool down to 20° C.
  5. filtrationthe crystalline precipitate was filtered off with suction
  6. washwashed with water
  7. customafter drying

Sources & evidence

ORD record
ord-31316ecad20647e7a4657e91a4b65c6e
Source dataset
uspto-grants-1997_08
Patent number
US05658933

Reaction notes

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