Ethyl 3-aminobenzoate → Ethyl 3-hydrazinylbenzoate

Participants

Reaction Steps

To a solution of m-aminobenzoic acid ethyl ester (200 g, 1.21 mmol) in conc. HCl (200 mL) was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mmol) at 0° C. and the reaction mixture was stirred for 1 h. A solution of SnCl2.2H2O (662 g, 2.92 mmol) in conc. HCl (2 L) was then added at 0° C. The reaction solution was stirred for 2 h at RT. The precipitate was filtered and washed with ethanol and ether to yield ethyl 3-hydrazinobenzoate, which was used for the next reaction without further purification.

Provenance & Evidence