Ammonia → HCID 15082734, compound

Participants

Reaction Steps

The phenylhydrazone of 2-methyl-1-indanone (1.44 g, 6.1 mmol) was heated in diethylene glycol (20 cm3) to near its reflux temperature, until ammonia started to evolve from the air condenser. Heating was continued overnight, or until the ammonia ceased to evolve. The solution was cooled, poured into an equal volume of water, and extracted into diethylether. The ethereal solution was back-extracted with 2M hydrochloric acid, which was made basic with sodium hydroxide, and re-extracted with diethylether. The extracts were evaporated and the residue was purified by column chromatography using silica eluating with 5% EtOAc petrol to yield the title compound as a colourless solid (Rf 30% EtOAc/petrol 0.8). Yield: (28%). M.p. 72° C. 1H NMR (CDCl3) δ: 1.46 (3H, s,), 3.10 (1H, d), 3.30 (1H, dd,), 4.05 (1H, s,), 4.69 (1H, s,), 6.52 (1H, dd,), 6.71 (1H, ddd,), 6.95 (1H, ddd,), 7.0-7.2 (5H, m,).

Provenance & Evidence