HCID 9951467, compound → 4-[N-(4-aminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole

HRID 1488491Notes

Reaction equation

HRID 1488491 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([N:17]2[CH:21]=[N:20][N:19]=[CH:18]2)[C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H]>[Ni].C(O)C>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:7]([N:17]2[CH:18]=[N:19][N:20]=[CH:21]2)[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:23][CH:22]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 9951467HCID 9951467, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 229058094-[N-(4-aminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazoleYield 32%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A catalytic amount of Raney nickel was added to 50 ml of an ethanol solution containing 3.74 g of 4-[N-(4-bromobenzyl)-N-(4-nitrophenyl) amino]-4H-1,2,4-triazole, and the mixture was stirred for about 2 hours in the presence of hydrogen gas at room temperature. After the catalyst was removed by filtration, the resulting filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 1.1 g of 4-[N-(4-aminophenyl)-N-(4-bromobenzyl)amino]-4H-1,2,4-triazole from the chloroform/methanol (50:1) eluate.

Workup

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

Sources & evidence

ORD record
ord-369e5e5fe0504009adede4b3e3cae243
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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