N-(3-nitrophenyl)acrylamide → N-(3-Aminophenyl)acrylamide

HRID 1815890Notes

Reaction equation

HRID 1815890 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:14])[CH:12]=[CH2:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Fe].O>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:14])[CH:12]=[CH2:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 12531248N-(3-nitrophenyl)acrylamide

Product 1

HCID 22033841N-(3-Aminophenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

For example, N-(3-nitrophenyl)acrylamide 2 is reduced in the presence of iron powder, FeSO4 and water, preferably upon heating, more preferably upon heating to reflux. The reaction mixture is cooled to RT and the solution is made basic, such as to a pH>12, preferably to a pH of about 13-14 to give N-(3-aminophenyl)acrylamide 3.

Workup

  1. temperaturepreferably upon heating
  2. temperaturemore preferably upon heating to reflux

Sources & evidence

ORD record
ord-2e288d0d39394bdba4d7362ed7b26497
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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