1,2-Dimethyl-3,5-dinitrobenzene → 2,3-Dimethyl-5-nitroaniline

HRID 618260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618260
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-])=O)[C:3]=1[CH3:14]>C(O)(=O)C>[CH3:14][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=1[NH2:11]

Komponenten

3

Edukt 1

HCID 1646961,2-Dimethyl-3,5-dinitrobenzene

Produkt 1

HCID 8207862,3-Dimethyl-5-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1,2-Dimethyl-3,5-dinitrobenzene (2.5 g, prepared as described in the above scheme) was dissolved in glacial acetic acid (25 mL, from Mallinckrodt) under N2 and heated to reflux. The heat source was removed and iron (2.13 g) was added all at once. After the initial vigorous reaction, the mixture was heated at reflux for 10 min and then cooled to room temperature. The reaction mixture was filtered through a celite pad and washed with ethyl acetate. The filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and refiltered through a celite pad and then washed with saturated sodium bicarbonate solution and half-saturated sodium chloride solution. After drying over magnesium sulfate and evaporation of the solvent, 2,3-dimethyl-5-nitro-phenylamine (1.41 g) was obtained.

Aufarbeitung

  1. temperatureheated to reflux
  2. customThe heat source was removed
  3. additioniron (2.13 g) was added all at once
  4. customAfter the initial vigorous reaction
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 10 min
  7. filtrationThe reaction mixture was filtered through a celite pad
  8. washwashed with ethyl acetate
  9. customThe filtrate was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. washwashed with saturated sodium bicarbonate solution and half-saturated sodium chloride solution
  12. dry with materialAfter drying over magnesium sulfate and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-6806b6ec0b0a47ddbc195bd5156ae56a
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952362

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