Water → 2,4-Dimethyl-5-nitroaniline

HRID 1106730

Reaktionsgleichung

Reaktionsgleichung von HRID 1106730
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH:12]C(=O)C.O.S(=O)(=O)(O)O>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH2:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 112848Acetamide, N-(2,4-dimethyl-5-nitrophenyl)-

Produkt 1

HCID 2280072,4-Dimethyl-5-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-(2,4-dimethyl-5-nitrophenyl)acetamide, water (24 mL), concentrated sulfuric acid (12 mL), and ethanol (120 mL) was heated at reflux under an atmosphere of nitrogen for 4 hours. The ethanol was evaporated under reduced pressure and the residue partitioned between ethyl acetate (250 mL) and brine (150 mL). The brine solution was reextracted with ethyl acetate. The combined ethyl acetate extracts were then dried over magnesium sulfate. Evaporation afforded a crude product which was flash chromatographed on silica and eluted with ethyl acetate:hexane (1:4) to afford 4.63 g as a pale yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for 4 hours
  3. customThe ethanol was evaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate (250 mL) and brine (150 mL)
  5. dry with materialThe combined ethyl acetate extracts were then dried over magnesium sulfate
  6. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-d80351a3127f41bc8ba186ed2b51f89f
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057349

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