52 g (0.240 mol, 1.1 equiv.) of diethoxymethylene malonate was added to meta-chloroaniline (30 g, 0.235 mol, 1.0 equiv.) and the reaction mixture was heated under stirring at 97-100 °C for 2 h. Under a nitrogen atmosphere, the warm acrylate was added dropwise into a hot solution of diphenyl ether (225 °C). The reaction mixture was stirred at 225 °C for 2 h followed by cooling to 50 °C. 100 mL of toluene was added to the semi-solid mass and the mixture was stirred well for 15 min. The product was filtered in vacuo, washed with toluene (2x 50 mL) and dried in the oven (40 °C) to afford 9 as a brown fluffy solid (54 g, 0.241 mol, 91%). mp = 294-296 °C (lit. = 295-297 °C). 27