Stannous chloride dihydrate → Ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride

Participants

Reaction Steps

To a solution of 3-aminonaphthalene-1-carboxylic acid ethyl ester (2 g, 9.3 mmol) in conc. HCl (2 mL) was added dropwise an aqueous solution of NaNO2 (0.63 g, 9.3 mmol) at 0° C. The resulted mixture was stirred for 1 h and then treated dropwise with a solution of SnCl2.2H2O (4.2 g, 18.6 mmol) in conc. HCl (10 mL) at 0° C. The reaction mixture was stirred for 2 h at RT. precipitate was collected and washed with EtOH and Et2O to yield ethyl 3-hydrazinonaphthalene-1-carboxylate hydrochloride as a white solid (1.5 g), which was used for the next reaction without further purification.

Provenance & Evidence