Sodium Hydroxide → N-(3-Aminophenyl)acrylamide

HRID 1815892Notes

Reaction equation

HRID 1815892 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.[OH-].[Na+]>CCOC(C)=O.O.[Fe]>[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

6

Reactant 2

HCID 14798Sodium HydroxideHCID 12531248N-(3-nitrophenyl)acrylamide

Product 1

HCID 22033841N-(3-Aminophenyl)acrylamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-nitrophenyl)-acrylamide (1.1 g, 5.61 mmol), iron powder (1.88 g, 33.7 mmol), FeSO4 (3.12 g, 11.2 mmol), Celite® (1.0 g) and H2O (45 mL) was heated to reflux with stirring for 2 h. The reaction mixture was cooled to RT and the solution was made basic to pH 13-14 by the addition of 2N NaOH. The reaction mixture was diluted with EtOAc and water. The solution was filtered to remove the solids and the solids were washed with EtOAc. The aqueous layer was extracted three times with EtOAc (100 mL) and the combined organics were dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography using EtOAc as the solvent to give N-(3-aminophenyl)acrylamide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe solution was filtered
  4. customto remove the solids
  5. washthe solids were washed with EtOAc
  6. extractionThe aqueous layer was extracted three times with EtOAc (100 mL)
  7. dry with materialthe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7dc910cd55db44ba9ea3adfe5c72402e
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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