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

HRID 745964Notes

Reaction equation

HRID 745964 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H][H]>[Ni].O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 540912824-[2-(3,4-Dichlorophenyl)ethenyl]nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 112541254-(3,4-Dichlorophenethyl)anilineYield 86.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(3,4-dichlorophenyl)ethenyl]nitrobenzene (34.0 g, 116 mmol) and 2 g of Raney nickel in 510 ml of tetrahydrofuran were shaken under hydrogen at 15 psi (103.4 kPascal) until four equivalents of hydrogen were consumed. The catalyst was removed by filtration, and the resulting filtrate evaporated in vacuo to yield a residual tan solid. Recrystallization from hexane yielded 26.6 g (86%) of 4-[2-(3,4-dichlorophenyl)ethyl]benzenamine, mp 72°-74° C.

Workup

  1. customwere consumed
  2. customThe catalyst was removed by filtration
  3. customthe resulting filtrate evaporated in vacuo
  4. customto yield a residual tan solid
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-661e43aa1bf549d0a0188e2333323516
Source dataset
uspto-grants-1986_07
Patent number
US04602023

Reaction notes

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