(4-Methoxy-3-nitro-phenyl)-trimethyl-silane → 2-Methoxy-5-trimethylsilanyl-phenylamine

HRID 23537Notes

Reaction equation

HRID 23537 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][C:4]=1[N+:13]([O-])=O.[H][H]>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][C:4]=1[NH2:13]

Participants

5

Reactant 2

HCID 22573859(4-Methoxy-3-nitro-phenyl)-trimethyl-silaneHCID 178418361HCID 178418361, compound

Product 1

HCID 225738682-Methoxy-5-trimethylsilanyl-phenylamineYield 60.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above trimethyl-silane (760 mg, 3.4 mmol) was dissolved in 25 mL of EtOH. To this was added 10% Pd/C (128 mg). The reaction was stirred for 12 h under a 1 atm balloon of hydrogen gas. The reaction was then filtered through diatomaceous earth and concentrated in vacuo to provide 400 mg (60%) of 2-methoxy-5-trimethylsilanyl-phenylamine as an amber oil which was used without further purification.

Workup

  1. filtrationThe reaction was then filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfffa89424a049628941747e8417d393
Source dataset
uspto-grants-2005_02
Patent number
US06852717B2

Reaction notes

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