2-Tetralone → HCID 58156756, compound

Participants

Reaction Steps

A mixture of 2-tetralone (2.00 mL, 14.7 mmol) and dimethylformamide dimethyl acetal (2.10 mL, 15.0 mmol) is heated to reflux for 14 h. The mixture is cooled and evaporated, and approximately half of the residue is dissolved in acetic acid (10 mL) and treated with 3-hydrazinobenzoic acid (750 mL, 4.93 mmol). The solution is heated to reflux for 12 h, then cooled and poured into water (100 mL). The resulting precipitate is collected by filtration, washed with water, and evaporated under high vacuum to afford the title compound (900 mg, 3.10 mmol, 63%) as a tan solid, m.p. 273-275° C. 1H NMR (300 MHz, DMSO-d6): δ 13.30 (1H, br), 8.15 (1H, s), 8.10 (1H, t, J=1.9 Hz), 7.95 (1H, dt, J=7.6, 1.3 Hz), 7.82 (1H, ddd, J=8.0, 2.2, 1.0 Hz), 7.66 (1H, t, J=7.9 Hz), 7.53 (1H, dd, J=7.6, 1.2 Hz), 7.26-7.22 (2H, m), 7.10 (1H, dt, J=7.3, 1.2 Hz), 3.05-3.02 (2H, m), 3.00-2.87 (2H, m). MS (ES+): m/e 292 (21), 291 (100). MS (ES−): m/e 290 (20), 289 (100).

Provenance & Evidence