4-Methyl-3-nitrobenzoic acid → HCID 2056375, compound

Participants

Reaction Steps

4-Methyl-3-nitrobenzoic acid (14.6 g, 81.0 mmol) was stirred in a solvent of dimethyl formamide (40 mL). The reaction solution was added with HATU (47.2 g, 124 mmol), DIPEA (32.5 mL, 186 mmol) and 3-(trifluoromethyl)aniline (7.72 mL, 62.1 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated solid was added with ethyl acetate, and stirred for 2 hours or more. The resulting solid was filtered under reduced pressure, and washed with ethyl acetate and methanol. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (14.9 g, 74%).

Provenance & Evidence