Water → N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.7 g, 3.2 mmol), N-(4-iodo-phenyl)-acetamide (1.4 g, 5.4 mmol), NaHCO3 (1.1 g, 12.8 mmol), Bu4NBr (1.2 g, 3.6 mmol) and Pd(OAc)2 (0.04 g, 0.2 mmol) in DMF (15 mL) was heated at 70° C. for 2 days. The cooled mixture was poured into water (150 mL) and was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). Solvent was removed and the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamide (0.4 g, 32%): mp 175-177° C.; 1H NMR (CDCl3) δ 7.51(d, J=8 Hz, 2H), 7.41 (s, 1H), 7.26 (d, J=9.0 Hz, 2H), 7.02-6.89 (m, 3H), 5.57 (s, 1H), 4.11-4.03 (q, J=7 Hz, 2H), 3.92 (s, 3H), 2.19 (s, 3H), 1.44 (t, J=7 Hz, 3H); 13C NMR (CDCl3) δ 168.38, 162.14, 150.93, 147.96, 139.91, 134.84, 129.58, 129.30, 123.08, 119.34, 118.53, 114.06, 111.01, 92.49, 64.53, 55.96, 24.65, 14.66; Anal Calcd for C20H20N2O3: C, 71.46; H, 5.99; N, 8.33. Found: C, 71.46, 6.01; N, 8.25.

Provenance & Evidence