2-(2-Nitrophenyl)-3-(trimethylsilyl)-2-propene → 2-(1-Methyl-2-trimethylsilylethyl)phenylamine

HRID 498918Notes

Reaction equation

HRID 498918 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[CH:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH2:12][Si:13]([CH3:15])([CH3:14])[CH3:16])[CH3:11]

Participants

5

Reactant 2

HCID 684549542-(2-Nitrophenyl)-3-(trimethylsilyl)-2-propeneHCID 178418361HCID 178418361, compound

Product 1

HCID 578833472-(1-Methyl-2-trimethylsilylethyl)phenylamineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The reaction product of step A [7.2 g] was hydrogenated in tetrahydrofurane over palladium on charcoal at atmospheric pressure and room temperature until the uptake of hydrogen ceased. The catalyst was filtered off and, after evaporation of the solvent, the product was chromatographed on silacagel (eluent: 10% ethylacetate in hexane) to yield 2-(2-aminophenyl)-3-(trimethylsilyl)-propane [4.7 g; 88% purity according to NMR]. This product was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customafter evaporation of the solvent
  3. customthe product was chromatographed on silacagel (eluent: 10% ethylacetate in hexane)

Sources & evidence

ORD record
ord-62388dac03b24cc1990f6196e9532ce6
Source dataset
uspto-grants-2010_08
Patent number
US07767623B2

Reaction notes

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