4'-Methyl-2-nitro-1,1'-biphenyl → 4'-Methyl-biphenyl-2-ylamine

HRID 374884Notes

Reaction equation

HRID 374884 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1>[Ni].CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenyl

Product 1

HCID 15108204'-Methyl-biphenyl-2-ylamineYield 92.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

3 g of Raney nickel are added to 23.9 g (0.112 mol) of 4'-methyl-2-nitrobiphenyl (R. B. Muller and S. Dugar, Organometallics 1984, 3, 1261) in 50 ml of methanol and the mixture is hydrogenated under normal pressure at room temperature until the theoretical amount of H2 has been absorbed. The catalyst is then removed by filtration and the filtrate is concentrated. Chromatography on SiO2 (500 g) using EA/HEP(1:6) as the eluent yields 19 g of the title compound as an oil (92.5%)

Workup

  1. customis hydrogenated under normal pressure at room temperature until the theoretical amount of H2
  2. customhas been absorbed
  3. customThe catalyst is then removed by filtration
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-2a6b508cc45b4f519792018238bd5ebf
Source dataset
uspto-grants-1996_01
Patent number
US05482957

Reaction notes

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