4-[2-(3-Fluoro-phenyl)-vinyl]-1-nitro-benzene → 4-[2-(3-Fluoro-phenyl)-vinyl]-phenylamine

HRID 1884155Notes

Reaction equation

HRID 1884155 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1>C(OCC)(=O)C.[Pt]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 686145784-[2-(3-Fluoro-phenyl)-vinyl]-1-nitro-benzene

Product 1

HCID 686147874-[2-(3-Fluoro-phenyl)-vinyl]-phenylamineYield 62%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.41 g (10 mmol) of 4-[2-(3-fluoro-phenyl)-vinyl]-1-nitro-benzene is dissolved in 25 ml of ethyl acetate and treated with 240 mg of platinum 5% on charcoal. Hydrogenation is performed at room temperature and normal pressure for 4 h. The catalyst is filtered off and the filtrate concentrated. The residue is crystallised from diethyl ether/heptane to yield 1.32 g (62%) of an orange solid. MS: m/e=213.1 (M+).

Workup

  1. customis performed at room temperature
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate concentrated
  4. customThe residue is crystallised from diethyl ether/heptane

Sources & evidence

ORD record
ord-58893d6715b74fb5ba03948d76b88cd1
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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