4-[2-(3,4-Dichlorophenyl)ethenyl]nitrobenzene → 4-(3,4-Dichlorophenethyl)aniline

HRID 488483Notes

Reaction equation

HRID 488483 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:4][C:3]=1[Cl:19]>O1CCCC1.[Ni]>[Cl:19][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 540912824-[2-(3,4-Dichlorophenyl)ethenyl]nitrobenzene

Product 1

HCID 112541254-(3,4-Dichlorophenethyl)anilineYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A sample of 1,2-dichloro-4-[2-(4nitrophenyl)ethenyl]benzene (98.0 g, 0.33 mol) in tetrahydrofuran (THF) (1.6 L) was reduced in the presence of Raney Nickel (Ra—Ni) (20 g) at 25° C. to 40° C. (ΔP=13.5 psi) under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated in vacuo to give an orange solid, 85.0 g (0.32 mol, 95.8%) of the desired product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b2c21524bbc048fb90da33b9e182a9e7
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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