Acetic Acid → 3-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid ethyl ester

HRID 2269768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269768
C(O)(=O)C.[CH2:5]([O:7][C:8](=[O:25])[C:9]([CH3:24])=[CH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[N+:21]([O-])=O)[CH3:6]>[Fe].O>[CH2:5]([O:7][C:8](=[O:25])[C:9]([CH3:24])=[CH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[NH2:21])[CH3:6]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 702169653-(4,5-Dimethoxy-2-nitrophenyl)-2-methyl-2-propenoic acid ethyl ester

Produkt 1

HCID 702131123-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid ethyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Into 250 ml of glacial acetic acid, 19.0 g of 3-(4,5-dimethoxy-2-nitrophenyl)-2-methyl-2-propenoic acid ethyl ester were dissolved; and, with 15.0 g of iron powder and 20 ml of ion-exchanged water being added thereto, the mixture was refluxed under heating for 40 minutes. The resulting reaction liquid was filtered out, the filtrate was concentrated under a reduced pressure, and thus obtained residue was dissolved in ethyl acetate. The resulting product was successively washed with water, a 5% aqueous sodium hydrogencarbon ate solution, and a saturated aqueous sodium chloride solution; and then was left on sodium sulfate anhydride for one night so as to be dried. Ethyl acetate was evaporated under a reduced pressure from this solution, and the resulting crude product was recrystallized from hexane/ethanol, whereby 12.5 g of the aimed product were obtained (yield: 78%).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 40 minutes
  3. customThe resulting reaction liquid
  4. filtrationwas filtered out
  5. concentrationthe filtrate was concentrated under a reduced pressure, and thus obtained residue
  6. dissolutionwas dissolved in ethyl acetate
  7. washThe resulting product was successively washed with water
  8. waitand then was left on sodium sulfate anhydride for one night so as
  9. customto be dried
  10. customEthyl acetate was evaporated under a reduced pressure from this solution
  11. customthe resulting crude product was recrystallized from hexane/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4c889f57288741eb805a246cf407934c
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329546B1

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