HCID 23233793, compound → HCID 23233794, compound

HRID 859220Notes

Reaction equation

HRID 859220 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[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:3]=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 23233793HCID 23233793, compound

Product 1

HCID 23233794HCID 23233794, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.41 g (10 mmol) (E)-1-fluoro-3-[2-(4-nitrophenyl)ethenyl]-benzene in 25 ml of ethyl acetate is flushed with argon and, thereafter, hydrogenated at RT and atmospheric pressure during 4 hours using 0.241 g of platinum on carbon (5%) as the catalyst. For the working-up, the catalyst is filtered over Dicalit and the resulting solution is evaporated under reduced pressure. The solid material obtained is crystallised from a mixture of ether and heptane to yield 1.32 g (62.5% of theory) of (E)-4-[2-(3-fluoro-phenyl)-vinyl]-phenylamine as an orange solid; MS: m/e=213 (M)+.

Workup

  1. filtrationthe catalyst is filtered over Dicalit
  2. customthe resulting solution is evaporated under reduced pressure
  3. customThe solid material obtained
  4. customis crystallised from a mixture of ether and heptane

Sources & evidence

ORD record
ord-b1b991da716147a195ebb58d4725b8cc
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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