Acetic Acid → HCID 14578865, compound

HRID 345427Notes

Reaction equation

HRID 345427 reaction equation
[CH3:1][C:2]1([CH3:16])[C:10]2[C:5](=[CH:6][C:7]([OH:14])=[C:8]([N+:11]([O-])=O)[CH:9]=2)[NH:4][C:3]1=[O:15].[H][H].[C:19](O)(=O)[CH3:20]>[Pd]>[N:4]1[CH:5]=[CH:6][C:19]([C:20]2[O:14][C:7]3[CH:6]=[C:5]4[NH:4][C:3](=[O:15])[C:2]([CH3:16])([CH3:1])[C:10]4=[CH:9][C:8]=3[N:11]=2)=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14578864HCID 14578864, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14578865HCID 14578865, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4 g. 1,3-Dihydro-3,3-dimethyl-6-hydroxy-5-nitro-2H-indol-2-one in 100 ml. glacial acetic acid were hydrogenated in the presence of 1 g. 10% palladium/charcoal at ambient temperature and normal pressure until 1.3 liters of hydrogen had been taken up. The catalyst was filtered off and 2.1 ml. 4-pyridinecarbaldehyde were poured into the filtrate, the solution thereby becoming yellow-orange coloured. While stirring, air was passed through the solution for 3 days, whereafter it was evaporated to dryness in a vacuum, the residue was digested with an aqueous solution of ammonia and water and purified by column chromatography (800 ml. silica gel; elution agent dichloromethane:methanolic ammonia=20:1 v/v). The appropriate fractions were evaporated in a vacuum and the crystalline residue was digested with ethanol and filtered off with suction to give 4.0 g. of beige crystals which were recrystallised from ethanol with treatment with fullers' earth. There were obtained 2.5 g. of the title compound in the form of colourless crystals; m.p. 336°-338° C. Yield 49% of theory.

Workup

  1. customat ambient temperature
  2. filtrationThe catalyst was filtered off
  3. addition4-pyridinecarbaldehyde were poured into the filtrate
  4. customwas evaporated to dryness in a vacuum
  5. custompurified by column chromatography (800 ml. silica gel; elution agent dichloromethane:methanolic ammonia=20:1 v/v)
  6. customThe appropriate fractions were evaporated in a vacuum
  7. filtrationfiltered off with suction
  8. customto give 4.0 g
  9. customof beige crystals which were recrystallised from ethanol with treatment with fullers' earth
  10. customThere were obtained 2.5 g

Sources & evidence

ORD record
ord-9f8894ab45b94290b6c786e068384d30
Source dataset
uspto-grants-1991_10
Patent number
US05057526

Reaction notes

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