Sulfuric Acid → HCID 67377568, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-(4-chloro-2-fluorophenyl)hydrazono)cyclohexanone (0.5 g, 1.9 mmol) in MeCN (5 mL), H2SO4 (0.31 mL, 5.9 mmol, 1.8M solution) was added slowly and the resulting mixture was heated to 80° C. for 12 h. The reaction mixture was cooled to room temperature, basified with saturated NaHCO3 (pH-8) and extracted with EtOAc (2×30 mL). The combined organic extracts were dried over sodium Na2SO4 and concentrated in vacuo to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant] to provide the title compound (120 mg, 25%). 1H NMR (200 MHz, CDCl3, δ in ppm): 8.96 (bs, 1H), 7.43 (d, J=1.0 Hz, 1H), 7.12 (dd, 1H, J=10.2, 1.60 Hz, 1H), 2.99 (t, J=5.8 Hz, 2H), 2.71 (t, J=6.0 Hz, 2H), 2.34-2.21 (m, 2H).

Provenance & Evidence