Hydrazine hydrate (1:1) → 7-(Benzyloxy)-1H-indole

Participants

Reaction Steps

Hydrazine hydrate (4.6 g, 92 mmol, 85% solution) was added to a mechanically stirred mixture of 1-[2-[2-nitro-3-(phenylmethoxy)phenyl]ethenyl]pyrrolidine and N-methyl-N-[2-[2-nitro-3-(phenylmethoxy)phenyl]ethenyl]methanamine (20 g, 61.8 mmol, crude product obtained as described in Step 2) and Raney-Nickel (5 g) in methanol (500 mL), care being taken to keep the temperature at 45°-50° C. Two additional portions of hydrazine hydrate (4.6 g each ) were added after 30 and 60 minutes, respectively. The temperature was maintained at 45°-50° C. for 5 hours. After stirring overnight at room temperature, the mixture was filtered off (Celite) and the filtrate was concentrated in vacuo. The residue (dark liquid) was purified by flash-chromatography (on silica Merck-60, dichloromethane-light petroleum ether 1:1) to yield pure 7-benzyloxyindole as an oil that solidifies upon standing (2.3-3.03 g, 17-22%, based upon different runs). A sample was recrystallized from petroleum ether as white needles, m.p. 62°-63° C. (Dictionary of Organic Compounds Vol III, p 3077, m.p. 67°-68° C., ligroin).

Provenance & Evidence