Hydrazine → HCID 178434212, compound

Participants

Reaction Steps

A solution of 1-[2-hydroxy-4-(4-hydroxyphenyl)napthalen-1-yl]ethanone (0.223 g, 0.8 mmol), and 35% aqueous hydrazine (0.72 mL, 8.0 mmol) in diethylene glycol (2.7 mL) was heated using a reflux condenser in a 170° C. oil bath for 12 h, then 190° C. for 2 h until 95% complete conversion was observed. The crude solution was purified directly via preparative reverse phase HPLC (CH3CN/H2O/TFA eluent) to give 0.132 g (60% yield) of 4-(1-methyl-3H-benzo[e]indazol-5-yl)phenol. 1H NMR (400 MHz, d6-DMSO): 9.62 (broad s, 1H), 8.37 (d, 1H), 7.82 (d, 1H), 7.65 (dt, 1H), 7.42 (dt, 1H), 7.39 (s, 1H), 7.30 (dd, 2H), 6.93 (s, 2H), 2.82 (s, 3H); MS (EI) for C18H14N2O: 275 (MH+).

Provenance & Evidence