Stannous Chloride → N,N-dimethyl-m-phenylenediamine

HRID 244523

Reaktionsgleichung

Reaktionsgleichung von HRID 244523
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[CH:4]=1.[Sn](Cl)Cl>C(O)C>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 69269N,N-Dimethyl-3-nitroaniline

Produkt 1

HCID 76084N,N-dimethyl-m-phenylenediamineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N,N-dimethyl-3-nitroaniline (3.00 g, 18.1 mmol) was dissolved in ethanol (40 cm3). Tin dichloride (16.3 g, 72.0 mmol) was added and the reaction heated under reflux for 16 h. The reaction mixture was allowed to cool before the bulk of the solvent was removed under reduced pressure. The remaining residue was poured in to water (100 cm3), and basified with sodium hydroxide (3M). The mixture was extracted with chloroform (3×30 cm3). The combined extracts were dried over sodium sulphate, filtered and the solvent removed under reduced pressure to give the product as a brown oil (2.01 g, 82%).

Aufarbeitung

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 16 h
  3. temperatureto cool before the bulk of the solvent
  4. customwas removed under reduced pressure
  5. additionThe remaining residue was poured in to water (100 cm3)
  6. extractionThe mixture was extracted with chloroform (3×30 cm3)
  7. dry with materialThe combined extracts were dried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-971757b34e2e402bbe2718b62e4a1ffd
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658665B2

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