HCID 12712917, compound → 3,5-Bis(trimethylsilyl)aniline

HRID 466323Notes

Reaction equation

HRID 466323 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=1)([O-])=O>C1C=CC=CC=1.[Pd]>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=1)[NH2:1]

Participants

4

Reactant 1

HCID 12712917HCID 12712917, compound

Product 1

HCID 146056423,5-Bis(trimethylsilyl)anilineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

1-Nitro-3,5-bis(trimethylsilyl)benzene (264 mg, 0.99 mmol) was catalytically hydrogenated over 10% Pd-C in 15 ml of benzene at atmospheric pressure for 135 minutes. The catalyst was filtered off and washed with benzene. The filtrate and washings were mixed and evaporated. The residue was purified by column chromatography on silica gel [eluent: methylene chloride-n-hexane (2:1)] to give 224 mg of light tan-colored low melting solid (yield 96%).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with benzene
  3. additionThe filtrate and washings were mixed
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel [eluent: methylene chloride-n-hexane (2:1)]

Sources & evidence

ORD record
ord-29d6f6addf804aa99f736c97a3b4e6e8
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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