4-(4-Methyl-1H-imidazol-1-yl)-2-nitroaniline → 2-Amino-4-(4-methyl-1H-imidazol-1-yl)aniline

HRID 535829Notes

Reaction equation

HRID 535829 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([N+:14]([O-])=O)[CH:8]=2)[CH:6]=1>CO.[Ni]>[NH2:14][C:9]1[CH:8]=[C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)[CH:13]=[CH:12][C:10]=1[NH2:11]

Participants

4

Reactant 1

HCID 867095594-(4-Methyl-1H-imidazol-1-yl)-2-nitroaniline

Product 1

HCID 100582902-Amino-4-(4-methyl-1H-imidazol-1-yl)anilineYield 95.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-(4-Methyl-1H-imidazol-1-yl)-2-nitroaniline (0.22 g, 1 mmol) was suspended in 20 mL of anhydrous methanol. The mixture was reduced with 0.11 g of Raney Ni at 40 psi for 7 hrs. Then the Raney Ni was removed by filtration. The filtrate was evaporated to give the title compound 0.18 g as a yellow solid (95.7%).

Workup

  1. customThen the Raney Ni was removed by filtration
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a677589cb8e245c7a3429733a4c884ed
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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