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

HRID 321984Notes

Reaction equation

HRID 321984 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-51524c40e72b4970b6bd8a86dfb3495d
Source dataset
uspto-grants-2001_04
Patent number
US06211178B1

Reaction notes

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