Nitrogen → 3-(2-Methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)aniline

Participants

Reaction Steps

3-Bromo-5-(trifluoromethyl)aniline (1.2 mL, 8.60 mmol) and 2-methylimidazole (847 mg, 10.3 mmol) were dissolved in dimethyl sulfoxide (8.6 mL), and CuI (490 mg, 2.58 mmol), 8-quinolinol (370 mg, 2.58 mmol) and potassium carbonate (2.38 g, 17.2 mmol) were added thereto. The reaction mixture was treated with N2 gas for 10 minutes to remove gas and subjected to a reaction at 120° C. for 12 hours. The reaction mixture was cooled to room temperature, and 14% aqueous ammonium hydroxide solution was added thereto. The reaction mixture was stirred for 1 hours at room temperature, diluted with ethyl acetate (30 mL) and washed with an aqueous sodium hydrogen carbonate solution (30 mL). The organic layer was washed with water, dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated mixture was filtered with a silica column using ethyl acetate to remove copper impurities, and the filtrate was distilled under reduced pressure. The concentrated mixture was crystallized with ethyl acetate (3 mL) and n-hexane (30 mL) to obtain the title compound (1.31 g) as a bright green solid.

Provenance & Evidence