Reacción #2439967

Ecuación de reacción

HCl

[2-Nitro-4-(4-nitrobenzoyl)phenyl] malonate

EtOH

→

6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

Rendimiento 51.0%

Disolventes

CHCl3

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturato reflux for 3 hours
3. 3
   Filtraciónfiltered while hot and
4. 4
   OtroThe cooled reaction mixture
5. 5
   Extracciónextracted once with H2O (400 mL)
6. 6
   Extracciónextracted with a 95% EtOAc/5% i-prOH solution (3×400 mL)
7. 7
   Secadodried over anhydrous Na2SO4
8. 8
   ConcentraciónThe solution was then concentrated in vacuo

Procedimiento

[2-Nitro-4-(4-nitrobenzoyl)phenyl] malonate (4.15 g, 9.61 mmol) was dissolved in EtOH (24 mL) after which Sn powder (9.16 g, 77 mmol) was added followed by dropwise addition of concentrated HCl(aq) (26 mL). The reaction mixture was allowed to reflux for 3 hours, filtered while hot and then allowed to cool to room temperature. The cooled reaction mixture was diluted with CHCl3 (400 mL) and then extracted once with H2O (400 mL). The aqueous layer was then neutralized with NaHCO3 (pH=7) and then extracted with a 95% EtOAc/5% i-prOH solution (3×400 mL). The organic layers were combined and dried over anhydrous Na2SO4. The solution was then concentrated in vacuo affording the 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one in 51% yield (1.24 g, 4.90 mmol).

Fuente