4-Methyl-3-nitroaniline → N-(4-methyl-3-nitrophenyl)-4-morpholino-3-(trifluoromethyl)benzamide

Participants

Reaction Steps

4-Morpholino-3-(trifluoromethyl)benzoic acid (694 mg, 2.523 mmol) was dissolved in dimethylformamide (5.6 mL), HATU (1.92 g, 5.047 mmol) and N,N-diisopropylethylamine (1.37 mL, 7.851 mmol) were added thereto and stirred at room temperature for 30 minutes. 4-Methyl-3-nitroaniline (256 mg, 1.682 mmol) was added to the reaction mixture and subjected to a reaction at 45° C. for 19 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (10 mL) and washed with an aqueous sodium hydrogen carbonate solution (10 mL). The organic layer was washed with water, dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated mixture was crystallized using ethyl acetate (3 mL) n-hexane (30 mL) to obtain the title compound (673 mg) as a brown solid.

Provenance & Evidence