Ethyl Acetate → 4-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline

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Reaction Steps

A mixture of 2-(2-chloro-5-nitro-phenyl)-5-phenyl-1H-imidazole (430 mg, 1.43 mmol) and tin (II) chloride dihydrate (1.15 g, 5.02 mmol) in EtOH (15 ml) is heated at reflux for 3 hours. The mixture is cooled down to room temperature and the solvent is removed in vacuo. The residue obtained is treated with ethyl acetate (80 ml) and 1N NaOH solution is added until the pH is raised to around 12. The suspension is kept stirring for 10 minutes and then filtered through Celite cake. The solution obtained is concentrated to yield 4-chloro-3-(5-phenyl-1H-imidazol-2-yl)-phenylamine as a dark red foam-like solid.

Provenance & Evidence