Reacción #60311

Ecuación de reacción

NH4Cl

THF

4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester

EtOH MeOH

→

clean desired product

Rendimiento 70.8%

4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester

Rendimiento 70.8%

Disolventes

CH2Cl2 THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic layer is washed with water (3×)
2. 2
   SecadoThe combined organic extracts are dried (Na2SO4)
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroThe solids are triturated with ether

Procedimiento

4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester 5c (0.50 g, 1.55 mmol) is dissolved into 2:1 EtOH/MeOH (15.5 mL). Saturated aqueous NH4Cl (15 mL), Zn powder (1.02 g, 15.6 mmol), and THF (10 mL) are added. After stirring for 20 hours, the reaction mixture is diluted with CH2Cl2/THF and water. The organic layer is washed with water (3×). The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure. The solids are triturated with ether to give 0.32 g (70%) clean desired product.

Fuente