4-Coumaric acid → HCID 820256, compound

Participants

Reaction Steps

To a stirred solution of 4-hydroxycinnamic acid (3.28 g, 20 mmol) in acetonitrile (40 ml) was added HOBt (3.24 g, 24 mmol) and EDC.HCl (4.6 g, 24 mmol). The mixture was stirred at room temperature for 2 h, and the resulting yellow suspension was cooled to 0° C. by an ice bath. A ice-cold solution of hydrazine (1.25 ml, 40 mmol) and cyclohexene (0.61 ml, 6 mmol) in acetonitrile (30 ml) was added into the suspension in one portion, and the mixture was stirred at 0° C. for 20 min, then all owed to warm to ambient temperature, with the stirring continued for additional 1 h. The yellow suspension was filtered off via suction, washed the solid successively with MeOH (3×30 ml), H2O (2×30 ml), saturated NaHCO3 (2×30 ml), H2O (2×20 ml) and EtOAc (2×20 ml), and air-dried to afford 133 (1.3 g, 36% yield) as yellow solid. 1H NMR (300 MHz, DMSO-d6): δ4.40 (brs, 3H), 6.32 (d, J=15.9 Hz, 1H), 6.76 (d, J=8.4 Hz, 2H), 7.33 (d, J=16.2 Hz, 1H), 7.36 (d, J=8.1 Hz, 2H), 9.21 (br s, 1H); 13C NMR (75 MHz, DMSO-d6): δ116.49, 117.21, 126.44, 129.83, 139.08, 159.72, 165.86; MS (ESI): m/z 179 (M+1).

Provenance & Evidence