HCID 601959, compound → 3-(Trimethylsilyl)aniline

HRID 1090418Notes

Reaction equation

HRID 1090418 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C1C=CC=CC=1.[Pd]>[CH3:11][Si:10]([CH3:13])([CH3:12])[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

4

Reactant 1

HCID 601959HCID 601959, compound

Product 1

HCID 124888833-(Trimethylsilyl)anilineYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

m-Nitrotrimethylsilylbenzene (200 mg) was catalytically hydrogenated over Pd-C in 7.5 ml of benzene at atmospheric pressure for 40 minutes. The catalyst was filtered off and washed with benzene and dry MeOH, successively. The filtrate and washings were mixed and evaporated. The residue was purified by column chromatography on silica gel [eluent: methylene chloride] to give 169 mg of pale brown liquid.

Workup

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

Sources & evidence

ORD record
ord-ab4926736b4a4afe870c4d8e79b7ac00
Source dataset
uspto-grants-1992_01
Patent number
US05081271

Reaction notes

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