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

HRID 1090421Notes

Reaction equation

HRID 1090421 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-d1641c3c909c4b689d25407378f566b1
Source dataset
uspto-grants-1992_01
Patent number
US05081271

Reaction notes

Loading…