Hydrogen Peroxide → HCID 178433905, compound

HRID 1954209Notes

Reaction equation

HRID 1954209 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[NH:3]1.[Se](=O)=O.OO>CO>[OH:7][C:5]1[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[N:3]=[C:2]([CH3:1])[C:6]=1[C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][CH:13]=2)[C:5]=1[OH:7]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24007Selenium DioxideHCID 23296378HCID 23296378, compound

Product 1

HCID 178433905HCID 178433905, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 3-methyl-1-(4-carboxyphenyl)-5-pyrazolidone (4.5 mmol) was dissolved in 20 ml of methanol and a sufficient amount of nitrogen gas was injected into the solution to replace the air with nitrogen. A catalytic amount of selenium dioxide (25 mg, 0.05 equivalent, MW 110.96) was added and 1.5 ml (3 equivalent) 30% hydrogen peroxide was added dropwise over an ice-cooled water bath. The mixture was stirred until room temperature. The stirring was continued for a further 12 hours while heating at 70-80° C. The deposited crystals were separated by filtration and dried under reduced pressure to obtain 460 mg of 5,5'-dihydroxy-3,3'-dimethyl-1,1'-bis(4-carboxyphenyl)-4,4'-bipyrazole (MW 434.12, 1.06 mmol, 47.1%).

Workup

  1. temperaturecooled water bath
  2. temperaturewhile heating at 70-80° C
  3. customThe deposited crystals were separated by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f113714c6a424d269714ef8e106a9b5d
Source dataset
uspto-grants-2000_09
Patent number
US06121305

Reaction notes

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