alpha-(3,4-Dichlorophenyl)-alpha-(2,6-dichloro-4-nitrophenyl)acetonitrile → 3,5-Dichloro-4-(3,4-dichloro-alpha-cyanobenzyl)aniline

HRID 1604310

Reaction equation

HRID 1604310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([N+:19]([O-])=O)=[CH:14][C:13]=2[Cl:22])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H][H]>CO.[Ni]>[Cl:18][C:17]1[CH:16]=[C:15]([CH:14]=[C:13]([Cl:22])[C:12]=1[CH:9]([C:10]#[N:11])[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[NH2:19]

Participants

5

Reactant 2

HCID 22008581alpha-(3,4-Dichlorophenyl)-alpha-(2,6-dichloro-4-nitrophenyl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 220085763,5-Dichloro-4-(3,4-dichloro-alpha-cyanobenzyl)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In 100 ml of methanol were dissolved 7.6 g of α-(3,4-dichlorophenyl)-α-(2,6-dichloro-4-nitrophenyl)acetonitrile and 0.8 g (50%) of Raney's nickel. The solution was subjected to reduction with three times as much mol. of hydrogen gas. Insolubles were removed from the reaction mixture, then the remaining solution was concentrated to give the titled compound in a yield of 95%, m.p. 191-194° C.

Workup

  1. customInsolubles were removed from the reaction mixture
  2. concentrationthe remaining solution was concentrated

Sources & evidence

ORD record
ord-3d6cc99aef8646acb4aa74eba9d5226e
Source dataset
uspto-grants-1999_11
Patent number
US05994355

Linked notes

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