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

HRID 2232168Notes

Reaction equation

HRID 2232168 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-7a7de5327cca42c4aa929c5af0a34328
Source dataset
uspto-grants-1988_11
Patent number
US04786755

Reaction notes

Loading…