4-[2-(4-Chloro-phenyl)-vinyl]-1-nitro-benzene → 4-[2-(4-Chlorophenyl)ethyl]aniline

HRID 1884161Notes

Reaction equation

HRID 1884161 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>C(OCC)(=O)C.[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

4

Reactant 1

HCID 1554154-[2-(4-Chloro-phenyl)-vinyl]-1-nitro-benzene

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.0 g (19.2 mmol) 4-[2-(4-chloro-phenyl)-vinyl]-1-nitro-benzene in 100 ml ethyl acetate is treated with 200 mg of platinum 5% on charcoal. Hydrogenation is performed at room temperature and normal pressure overnight. The catalyst is filtered off and the filtrate evaporated to yield 3.17 g (71%) of a slightly yellow solid. MS: m/e=231.9 (M++H).

Workup

  1. customis performed at room temperature
  2. customnormal pressure overnight
  3. filtrationThe catalyst is filtered off
  4. customthe filtrate evaporated
  5. customto yield 3.17 g (71%) of a slightly yellow solid

Sources & evidence

ORD record
ord-5dc1439ae2454ee38d02247b8ffc9d41
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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