5-Amino-2-chlorobenzoic acid → 2-Chloro-5-hydrazinylbenzoic acid hydrochloride

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Reaction Steps

A solution of 5-amino-2-chlorobenzoic acid (10.3 g, 60 mmol) in concentrated HCl at 0° C. is treated with an aqueous solution of NaNO2 (4.8 g, 70 mmol) at a rate to maintain a reaction temperature of <10° C., stirred for 0.5 h at 0° to 10° C., treated with a solution of tin chloride dihydrate (33.9 g, 150 mmol) in aqueous HCl at a rate to maintain a reaction temperature of <10° C., aqueous HCl is added periodically, as needed to facilitate stirring, stirred at 5° C. for an additional 1 h and filtered. The filtercake is recrystallized from water to afford the title product as white crystals, 9.6 g (71% yield), identified by HNMR analysis.

Provenance & Evidence