HCID 10490701, compound → 4-[N-acetyl-N-(4-aminophenyl)amino]-4H-1,2,4-triazole

HRID 1488496Notes

Reaction equation

HRID 1488496 reaction equation
[C:1]([N:4]([N:14]1[CH:18]=[N:17][N:16]=[CH:15]1)[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>[C].[Pd].CO>[C:1]([N:4]([N:14]1[CH:15]=[N:16][N:17]=[CH:18]1)[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10490701HCID 10490701, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 106802764-[N-acetyl-N-(4-aminophenyl)amino]-4H-1,2,4-triazoleYield 98.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A proper amount of 10% palladium-carbon was added to 15 ml of a methanol solution containing 0.38 g of 4-[N-acetyl-N-(4-nitrophenyl)amino]-4H-1,2,4-triazole and the mixture was subjected to catalytic reduction in the presence of hydrogen gas at room temperature for about 40 minutes. After completion of reaction, the catalyst was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 0.33 g of 4-[N-acetyl-N-(4-aminophenyl)amino]-4H-1,2,4-triazole from the chloroform/methanol (50/1) eluate.

Workup

  1. customAfter completion of reaction
  2. customthe catalyst was removed by filtration
  3. concentrationthe resulting filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-543030bbd0e1499cb92b902e63405881
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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