Tin tetrachloride → (2-Benzyloxy-phenyl)-hydrazine

Participants

Reaction Steps

The 2-benzyloxyaniline (4.99 g, 25.0 mmol) partially dissolved in conc hydrochloric acid (15 mL) was cooled to less than 0° C. and a solution of the sodium nitrite (2.07 g, 30.0 mmol) in water (10 mL) was added dropwise. The reaction was stirred at the same temp for 30 min, when tin chloride (16.9 g, 75.0 mmol) in hydrochloric acid (10 mL) was added dropwise again keeping temp ca 0° C. The reaction was stored overnight in the fridge. The aqueous was decanted off the resulting black oily gum and triturated with sat NaCl (cf. 50 mL) and then ether:hexane 1:2 (50 mL) before neutralising with 10M NaOH (aq) with external cooling and extracted into ether (2×100 mL). The combined ether layers were washed with water (100 mL) dried (MgSO4) and evaporated to give a brown oil which crystallised on standing (4.52 g, 84%). Material was used crude without further purification.

Provenance & Evidence