3-Ethoxyacryloyl chloride (84.7 g, 0.63 mol) was slowly added dropwise to a tetrahydrofuran (THF, 600 mL) solution of 2-chloro-6-methylaniline (59.5 g, 0.42 mol) and pyridine (68 ml, 0.63 mol) cooled to 0-5°C with stirring, maintaining the reaction temperature at 0-5°C. After completion of the drop, the reaction mixture was gradually warmed to 20°C and stirring was continued for 2 hours. Subsequently, the reaction solution was cooled to 0-10°C and acidified by slowly adding 1N hydrochloric acid (115 mL). The reaction mixture was diluted with water (310 mL) and concentrated under reduced pressure to a thick slurry. The thick slurry was diluted with toluene (275 mL) and stirred at 20-22°C for 15 minutes, then continued stirring at 0°C for 1 hour. The precipitated solid was collected by vacuum filtration, washed with water (2 x 75 mL) and dried to give (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide 74.1 g in 73.6% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (100 MHz, CDCl3) with the following data: 1H NMR δ 1.26 (t, 3H, J=7Hz), 2.15 (s, 3H), 3.94 (q, 2H, J=7Hz), 5.58 (d, 1H, J=12.4Hz), 7.10- 7.27 (m, 2H), 7.27-7.37 (d, 1H, J=7.5Hz), 7.45 (d, 1H, J=12.4Hz), 9.28 (s, 1H); 13C NMR δ 14.57, 18.96, 67.17, 97.99, 126.80, 127.44, 129.07, 131.32. 132.89, 138.25, 161.09, 165.36.
