4'-Nitro-[1,1'-biphenyl]-2-carbonitrile → 2-(4-Aminophenyl)benzonitrile

HRID 1898896Notes

Reaction equation

HRID 1898896 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)#[N:2]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])=[CH:14][CH:13]=1

Participants

5

Reactant 1

HCID 127147954'-Nitro-[1,1'-biphenyl]-2-carbonitrile

Product 1

HCID 13939262-(4-Aminophenyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.0 g (26.8 mmol) of 2'-cyano-4-nitrobiphenyl (prepared according to B. Sain, J. S. Sandhu, J. Org. Chem. 1990, 55, 2545) were dissolved in a mixture of 60 ml ethanol and 60 ml ethyl acetate, and the solution was filled into an autoclave. After addition of 660 mg 10% Pd on charcoal the mixture was set under an atmosphere of hydrogen (2-3 bar). The reduction was carried out at room temperature, the course of the reaction monitored by thin layer chromatography, and it had completed after 2.5 h. The catalyst was filtered and the solvent distilled off in vacuo. The title amine was obtained by crystallization from hexane as a white powder, m.p. 98°-100° C.

Workup

  1. additionthe solution was filled into an autoclave
  2. customwas carried out at room temperature
  3. filtrationThe catalyst was filtered
  4. distillationthe solvent distilled off in vacuo

Sources & evidence

ORD record
ord-402767aef9c44f979c8b6bfaf1d43922
Source dataset
uspto-grants-1996_11
Patent number
US05571813

Reaction notes

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