1,2-Cyclohexanedione → HCID 67378120, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydrazinylbenzonitrile hydrochloride (3 g, 17.6 mmol) dissolved in MeOH (30 mL), was heated to 60° C., and 1,2-cyclo hexadione (1.98 g, 17.6 mmol) in AcOH (30 mL) and HCl (12 mL) were added while maintaining the temperature at 60° C. The reaction mixture was stirred at 60° C. for 12 h and then cooled to room temperature. The volatiles were removed in vacuo and the residue was diluted with water, neutralized with saturated NaHCO3 solution and extracted with EtOAc (2×40 mL). The combined organic extracts were concentrated under reduced pressure to give the crude product which was purified by silica gel chromatography [EtOAc-hexane (1:3) as eluant] to provide the title compound (3.3 g, 89%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.80 (bs, 1H), 7.80 (d, J=2.0 Hz, 1H), 7.45 (dd, J=12.0, 2.0 Hz, 1H), 7.30 (d, J=12.5 Hz, 1H), 2.90 (t, J=9.0 Hz, 2H), 2.62 (t, J=9.0 Hz, 2H), 2.25 (m, 2H).

Provenance & Evidence