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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 216584Erstellt: 26. Oktober 2026

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

https://huagongshe.com/reaction/216584

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTetrahydrofuranHCID 8028—
EduktAmmonium ChlorideHCID 25517—
EduktEthanol, mixt. with methanolHCID 18681192—
Edukt4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl esterHCID 85868196—
KatalysatorZincHCID 23994—
LösungsmittelWaterHCID 962—
LösungsmittelTetrahydrofurane dichloromethaneHCID 21919333—
Produkt4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl esterHCID 8586819870,8%

Reaktionsschritte

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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08193230B2
Quelldatensatzuspto-grants-2012_06
ORD IDord-258a19d17bc44c7db698d78666e76602
Quellennotizuspto-grants-2012_06