4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamine → 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine

HRID 1886354Notes

Reaction equation

HRID 1886354 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([N+:17]([O-])=O)[CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[H][H]>[Ni].C(O)C>[N:1]1([CH:6]([C:10]2[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:7]([CH3:8])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 145184254-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamineHCID 178418361HCID 178418361, compound

Product 1

HCID 145184264-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 31 parts of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamine and 240 parts of ethanol was hydrogenated at 0.5.105Pa in a Parr apparatus and at room temperature with 30 parts of Raney nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth and the filtrate was evaporated, yielding 27.4 parts (100%) of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine as a residue (interm. 117).

Workup

  1. customat room temperature
  2. filtrationthe catalyst was filtered off over diatomaceous earth
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d7dbd2c91e534097b3920ebfd2d6d9b7
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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