Sodium Hydroxide → N-(5-amino-2-methoxyphenyl)-acrylamide

HRID 1815929Notes

Reaction equation

HRID 1815929 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[NH:12][C:13](=[O:16])[CH:14]=[CH2:15].[OH-].[Na+]>CCOC(C)=O.O.[Fe]>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH:12][C:13](=[O:16])[CH:14]=[CH2:15])[CH:5]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 882710HCID 882710, compound

Product 1

HCID 22496104N-(5-amino-2-methoxyphenyl)-acrylamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(2-methoxy-5-nitro-phenyl)-acrylamide (Step 1) (335 mg, 1.51 mmol), iron powder (0.51 g, 9.0 mmol), FeSO4 (839 mg, 3.02 mmol), Celite® (0.3 g) and water (9 mL) was heated to reflux with stirring for 3 h. The reaction mixture was cooled to RT. 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 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-(5-amino-2-methoxyphenyl)-acrylamide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe solution was filtered
  4. customto remove the solids and solids
  5. washwere 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-faea98bc3724433c898a1fdc89649584
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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