Reaktion #60311

Reaktionsgleichung

NH4Cl

THF

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

EtOH MeOH

→

clean desired product

Ausbeute 70.8%

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

Ausbeute 70.8%

Lösungsmittel

CH2Cl2 THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer is washed with water (3×)
2. 2
   TrocknenThe combined organic extracts are dried (Na2SO4)
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe solids are triturated with ether

Vorschrift

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.

Quelle