4-Chloro-4'-nitrostilbene → 4-[2-(4-Chlorophenyl)ethyl]aniline

HRID 1823059Notes

Reaction equation

HRID 1823059 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][CH:3]=1>[Pt]>[Cl:1][C:2]1[CH:3]=[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]=1

Participants

3

Reactant 1

HCID 59051974-Chloro-4'-nitrostilbene

Product 1

HCID 131358184-[2-(4-Chlorophenyl)ethyl]aniline

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

In an analogous manner to that described in Example 36b), the hydrogenation of (E)-1-chloro-4-[2-(4-nitrophenyl)ethenyl]-benzene using platinum on carbon (5%) as the catalyst but with a reaction time of 18 hours and simultaneous reduction of the double bond yields the 4-[2-(4-chloro-phenyl)-ethyl]-phenylamine as a light yellow solid; MS: m/e=232 (M+H)+.

Sources & evidence

ORD record
ord-863ea8c562f545f2a2142612f226666e
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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