2-Indanone → Indole

Participants

Reaction Steps

2-Indanone (5.25 g, 39.7 mmol) and phenylhydrazine hydrochloride (5.74 g, 39.7 mmol), were heated to reflux in glacial acetic acid (60 cm3) for 1 hour, and then cooled. The solution was poured into ice/water, and the solid precipitate collected by filtration. After partial purification by column chromatography, and crystallization (charcoal) from ethyl acetate to yielded colourless needles of the title compound. Yield 0.64 g (80%). M.p. 205° C. 1H NMR (DMSO-d6) δ: 3.65 (2H, s,), 7.0-7.2 (8H,), 10.40 (1H, br,).

Provenance & Evidence