Reacción #40454

ord-a8a6e596c40a42de81190832f7c60776

Ecuación de reacción

N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1
3-(2-nitrophenoxy)benzonitrile
O.O.[Cl][Sn][Cl]
SnCl2.2H2O
N#Cc1cccc(Oc2ccccc2N)c1
3-(2-aminophenoxy)benzonitrile
Rendimiento 99.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaat reflux for 4 h
  2. 2
    OtroThe volatile was evaporated
  3. 3
    workup.DISSOLUTIONthe residue was redissolved in EtOAc
  4. 4
    Lavadowashed with saturated aqueous NaHCO3 and 1N NaOH
  5. 5
    SecadoThe organic layer was dried over MgSO4
  6. 6
    Filtraciónfiltered
  7. 7
    Otroevaporated

Procedimiento

A solution of 3-(2-nitrophenoxy)benzonitrile (1.21 g, 5 mmol, 1.0 equiv) in 30 mL of EtOH was treated with SnCl2.2H2O (3-38 g, 3 equiv) at reflux for 4 h. The volatile was evaporated and the residue was redissolved in EtOAc, washed with saturated aqueous NaHCO3 and 1N NaOH. The organic layer was dried over MgSO4, filtered and evaporated to give 3-(2-aminophenoxy)benzonitrile (1.04 g, 99%). MS found for C13H11N2O (M+H)+: 211.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07727981B2uspto-grants-2010_06