Using 2-acetylpyrrole and a couple of aromatic amines, such as 3-chloroaniline and 4-chloroaniline as the raw materials, two chloroaniline based mono(imino)pyrroles 2-{1-[(3-chlorophenyl)l)imino]ethyl}pyrrole (1a) and 2-{1-[(4-chlorophenyl)l)imino]ethyl} pyrrole (1b) were prepared under the microwave irradiation. No indication showed the reaction occurred between 2-acetylpyrrole and 2-chloroaniline. These structures were characterized by X-ray single crystal diffraction, 1H NMR, IR, MS and elemental analysis. 1a belongs to monoclinic system, space group C2/C with a = 23.722 (15) Å, b = 5.720 (4) Å, c = 16.868 (11) Å, β = 98.404 (10)°, V = 2264 (3) Å3, Z = 8, Dc = 1.283 g·m-3, R1 = 0.0419, ωR2 = 0.1195. 1b also belongs to monoclinic system, space group P21/C with a = 13.323 (3) Å, b = 9.802 (2) Å, c = 9.107 (2) Å, β = 109.212 (4)°, V = 1123.1 (4) Å3, Z = 4, Dc =1.293 g·m-3, R1 = 0.0472, ωR2 = 0.1189. Reaction mechanism between the position of deactivation group on the aromatic amines and the Schiff base condensation was also discussed.