1-Naphthylamine → Hydrazine, 1-naphthalenyl-

Beteiligte Stoffe

Reaktionsschritte

Sodium nitrite (4.8 g) in water (20 ml) was added over 15 minutes to a stirred ice-cold suspension of 1-naphthylamine (9.58 g) in 6 M hydrochloric acid (80 ml). After an additional 30 minutes in the ice bath,, stannous chloride (44.5 g) in 6 M hydrochloric acid (80 ml) was added slowly and the resulting suspension was stirred at 0° for 3 hr. The resulting solid was filtered off and dissolved in a mixture of 40% potassium hydroxide solution (100 ml) and ethyl acetate (150 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried and concentrated under reduced pressure to afford the title compound as a purple solid (10.58 g Rf =0.1 in EA/CH (1/4)). I.R. (cm-1):3312-3474(NH and NH2); 1580-1610,(C=C)

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