1-Nitro-3-[2-(trimethylsilyl)ethynyl]-benzene → 3-[2-(Trimethylsilyl)ethynyl]aniline

HRID 1016386Notes

Reaction equation

HRID 1016386 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=1)([CH3:4])[CH3:3]>CC(O)C>[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 114700401-Nitro-3-[2-(trimethylsilyl)ethynyl]-benzene

Product 1

HCID 111597943-[2-(Trimethylsilyl)ethynyl]anilineYield 93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of the nitro compound, 3-[(trimethylsilyl)ethynyl]nitrobenzene, prepared as described above (0.86 g, 3.92 mmol) in 2-propanol (30 mL) was degassed with nitrogen and treated with 5% platinum on alumina (268 mgs). The mixture was shaken under an atmosphere of hydrogen (30 psi) on a Parr shaker apparatus for 22 hours. The reaction mixture was filtered through a short pad of Celite™ (diatamaceous earth) and concentrated by evaporation to give an oil which was dried in vacuo overnight to give the title product (692 mg, 93%) as a yellow brown oil.

Workup

  1. customprepared
  2. customwas degassed with nitrogen
  3. additiontreated with 5% platinum on alumina (268 mgs)
  4. filtrationThe reaction mixture was filtered through a short pad of Celite™ (diatamaceous earth)
  5. concentrationconcentrated by evaporation
  6. customto give an oil which
  7. customwas dried in vacuo overnight

Sources & evidence

ORD record
ord-e57df4bad2ba405dabf63ba50e98359f
Source dataset
uspto-grants-2002_11
Patent number
US06476040B1

Reaction notes

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