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

HRID 1808295Notes

Reaction equation

HRID 1808295 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-d052c0d53109463aa8f7fef434d0f715
Source dataset
uspto-grants-2013_01
Patent number
US08357816B2

Reaction notes

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