Clean a round-bottom flask with mag

Clean a round-bottom flask with magnetic stir-bar and oven-dried.Dissolve the 2-chloronicotinoyl chloride (185 mg) and 4-chloroaniline (128 mg) in tetrahydrofuran (5 mL per 1 mmol reagent) to make two solutions.Introduce the solution of aniline to the flask.Stir the solution in ice bath at 0 °C for 5 minutes.Add triethylamine (1 equivalent) to the solution of aniline followed by addition of the solution of acyl chloride drop by drop at 0 °C.Stir the resulting reaction mixture at room temperature overnight.Remove the ice bath.Filter the resulting product twice to remove the solid.Wash the resulting product with THF.Remove the tetrahydrofuran from the solution of crude product by vacuum.Absorb the residue on silica gel.Purify the residue by column chromatography (Combi flash® Rf).Dry the purified product under vacuum.