4-Coumaric acid → HCID 820256, compound

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).

1. temperaturethe resulting yellow suspension was cooled to 0° C. by an ice bath
2. stirringthe mixture was stirred at 0° C. for 20 min
3. temperatureto warm to ambient temperature, with the stirring
4. waitcontinued for additional 1 h
5. filtrationThe yellow suspension was filtered off via suction
6. washwashed 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)
7. customair-dried

ORD record

ord-09835144cfd0448594906d40ea0dba97

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260382B2