3-Nitrostyrene → 3-Aminostyrene

HRID 2072333Notes

Reaction equation

HRID 2072333 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8])([O-])=O>CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8]

Participants

3

Reactant 1

HCID 685143-Nitrostyrene

Product 1

HCID 42600413-AminostyreneYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

50 g of 3-nitrostyrene are dissolved in 240 g of methanol. 10 g of an 18% strength suspension of CoS3 in methanol are added to the solution. The mixture is heated to 100° C in the presence of 30 bars of H2 in a stainless steel autoclave. After 5 hours, the absorption of hydrogen is complete. The mixture is heated for a further half hour to 110° C at 30 bars of H2. 0.5 g of tert.-butyl-pyrocatechol is added to the cooled contents of the autoclave, the mixture is filtered and the solvent is distilled off. 37 g of 3-aminostyrene are obtained. Boiling point16 = 113° -115° C, ND20 = 1.6102.

Workup

  1. additionare added to the solution
  2. customthe absorption of hydrogen
  3. temperatureThe mixture is heated for a further half hour to 110° C at 30 bars of H2
  4. addition0.5 g of tert.-butyl-pyrocatechol is added to the cooled contents of the autoclave
  5. filtrationthe mixture is filtered
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-a3a81e86d3ff45489a791c79e1e35f28
Source dataset
uspto-grants-1977_09
Patent number
US04051177

Reaction notes

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