[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[CH:12]=[CH2:13])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>CCOC(C)=O.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:14])[CH:12]=[CH2:13])=[CH:8][CH:9]=1A mixture of N-(4-nitrophenyl)-acrylamide (Step 1) (0.203 g, 1.06 mmol), Iron powder (0.354 g, 6.34 mmol), FeSO4 (0.587 g, 2.11 mmol), Celite® (0.2 g) and water (6 mL) was heated to reflux with stirring for 3 h. The reaction mixture was cooled to RT and the solution was made basic to pH 13-14 by the addition of 2 N NaOH. The reaction mixture was diluted with EtOAc and water. The solution was filtered to remove the solids and solids washed with EtOAc. The aqueous layer was extracted three times with EtOAc (25 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-(4-aminophenyl)-acrylamide.
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