Ethanol → 1-(2-Ethoxyethyl)-1,2-phenylenediamine

HRID 637011

Reaktionsgleichung

Reaktionsgleichung von HRID 637011
C(OCC[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)C.C(O)C.[OH-].[Na+].[C:21]([O:24][CH2:25][CH3:26])(=O)[CH3:22]>O.[Zn]>[CH2:21]([O:24][CH2:25][CH2:26][C:7]1([NH2:6])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]1[NH2:13])[CH3:22]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 13623317N-(2-Ethoxyethyl)-2-nitroaniline

Produkt 1

HCID 698342721-(2-Ethoxyethyl)-1,2-phenylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Combine N-(2-ethoxyethyl)-2-nitroaniline (85.4 g, 406 mmol) and ethanol (300 mL). Add a solution of sodium hydroxide (6 g) in water (60 mL). Heat to reflux. Remove the heating and add portionwise zinc metal (106 g, 1.62 mol) at a rate such that the reaction is maintained at reflux. After the addition of zinc metal is complete stir for 30 minutes. Filter the reaction mixture and rinse with water. Extract the filtrate three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give 1-(2-ethoxyethyl)-1,2-phenylenediamine.

Aufarbeitung

  1. temperatureHeat to reflux
  2. customRemove the heating and
  3. temperatureis maintained
  4. temperatureat reflux
  5. filtrationFilter the reaction mixture
  6. washrinse with water
  7. extractionExtract the filtrate three times with ethyl acetate
  8. dry with materialDry the combined organic layers over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-d2fa34647c824c04bebadaa385bf69df
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194406B1

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