Stannous Chloride → 4-Amino-3-methylbenzonitrile

HRID 2753

Reaktionsgleichung

Reaktionsgleichung von HRID 2753
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]

Komponenten

6

Edukt 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 28014343-Methyl-4-nitrobenzonitrile

Produkt 1

HCID 70103164-Amino-3-methylbenzonitrileAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 h, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a solution of saturated NaHCO3. The solution is diluted with EtOAc and the resulting mixture is filtered through Celite. The filtered solution is separated. The organic layer is dried over MgSO4, filtered and concentrated to give the title compound (1.57 g, 8.7 mmol) as an off-white solid.

Aufarbeitung

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux
  3. temperaturethe solution is cooled to ambient temperatures
  4. filtrationthe resulting mixture is filtered through Celite
  5. customThe filtered solution is separated
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-68a8e77da56c464fb8e4488b01b277d1
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731315

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