2-Naphthylamine → 2-Naphthylhydrazine hydrochloride

Participants

Reaction Steps

NaNO2 (578 mg, 8.38 mmol) in H2O (1.2 mL) was slowly added (2 min of addition) over a suspension of 2-naphthylamine (800 mg, 5.59 mmol) in HCl ac. 6.0 M (6 mL) cooled in a H2O-ice bath. The resulting solution was stirred in H2O-ice bath for 1 h, and SnCl2 (3.71 g, 19.56 mol) was added slowly (5 min of addition). The resulting suspension was stirred in H2O-ice bath for 3.5 h, and then filtered. The solid was successively washed with H2O at 0° C. (4×8 mL), with H2O at rt (1×8 mL), with Et2O at 0° C. (2×4 mL), with Et2O/hexane (1:1, 2×4 mL) and with hexane (2×5 mL). The solid was dried to yield 690 mg of the desired product (Rf=0.7 (40% AcOEt/hexane), cream solid, 63% yield).

Provenance & Evidence