HCID 54204816, compound → HCID 18962542, compound

HRID 654391Notes

Reaction equation

HRID 654391 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:17]([O-])=O)=[C:5]([CH:11]=[C:12]([O:15][CH3:16])[C:13]=1[OH:14])[CH:6]=[CH:7][N+]([O-])=O>C(O)C.C(O)=O.[OH-].[OH-].[Pd+2]>[CH3:16][O:15][C:12]1[CH:11]=[C:5]2[C:4](=[C:3]([O:2][CH3:1])[C:13]=1[OH:14])[NH:17][CH:7]=[CH:6]2

Participants

5

Reactant 1

HCID 54204816HCID 54204816, compound

Product 1

HCID 18962542HCID 18962542, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 284Formic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 10 g (0.037 mole) of 3,5-dimethoxy-4-hydroxy-2,β-dinitrostyrene and 10 g of palladium hydroxide on charcoal in 400 cm3 of ethanol and 7 cm3 of formic acid is heated under reflux for 3 hours. After cooling, the reaction mixture is filtered through Celite. The filtrate is evaporated to dryness. The residue is redissolved in dichloromethane and the solution is filtered on silica gel. After distillation of the solvent under reduced pressure and recrystallization from diisopropyl ether, 1 g of the desired product is obtained in the form of a whitish solid (yield=14%).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered through Celite
  5. customThe filtrate is evaporated to dryness
  6. dissolutionThe residue is redissolved in dichloromethane
  7. filtrationthe solution is filtered on silica gel
  8. distillationAfter distillation of the solvent
  9. customunder reduced pressure and recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-1ecb41a2687a4acfa996aaf0ba0e83e6
Source dataset
uspto-grants-1992_07
Patent number
US05131911

Reaction notes

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