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ChemicalBook CAS DataBase List 4-(5-BROMO-1 H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE
519042-70-7

4-(5-BROMO-1 H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE synthesis

4synthesis methods
-

Yield:519042-70-7 82%

Reaction Conditions:

with hydrogenchloride;iron in ethanol;water;Reflux;

Steps:



General procedure: Iron powder (3-4 mmol) and 6 N HCl solution (1 ml) were added to the solution of the nitro derivatives (1 mmol) in EtOH (5 ml) and the mixture was heated to reflux under nitrogen for 3-5 h. After cooling to room temperature, the suspension was diluted with EtOAc (20 ml); a solution of 6 M NaOH (20 ml) was added until basic pH and the layers were separated. The aqueous layer was extracted with AcOEt(2 X 20 ml) and the combined organic layers were washed with brine,dried over anhydrous Na2SO4, filtered and evaporated under vacuum.The crude product was purified by chromatography on silica gel(eluent: EtOAc/Hexane 6:4 v/v or CHCl3/MeOH 9.5:0.5 v/v to 9:1 v/v)or triturated with diethyl ether.

References:

Agamennone, Mariangela;Caradonna, Alessia;Di Pizio, Antonella;Laghezza, Antonio;Loiodice, Fulvio;Luisi, Grazia;Piemontese, Luca;Tortorella, Paolo [Bioorganic and medicinal chemistry,2019]