Ethanol → HCID 59256628, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tin (II) chloride hydrate (8.8 g, 0.039 mol), 4,6-dichloro-N-(4-fluorophenyl)-3-hydroxy-2-nitrobenzamide (2.7 g, 0.008 mol) and EtOH (70 mL) was heated at 70° C. for 1 h and left to cool to room temperature. The mixture was poured onto ice, basified to pH 8 (sat'd NaHCO3), and stirred at room temperature for 1.5 h before re-acidifying to pH 6.5 with glacial HOAc. The suspension was filtered; the filtrate was concentrated to give a beige solid. The beige solid was combined with the filter cake and extracted with hot ethyl acetate (5×). The extracts were combined to provide 2-amino-4,6-dichloro-N-(4-fluorophenyl)-3-hydroxybenzamide as a solid (2.0 g, 79%).

Provenance & Evidence