3-Nitroaniline → HCID 68419705, compound

Participants

Reaction Steps

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (7.85 g, 41.5 mmol) in tetrahydrofuran (80 mL) were added N,N-dimethylformamide (50 μL) and oxalyl chloride (4.33 mL, 49.8 mmol), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure to give 3-(cyano-1-methylethyl)benzoyl chloride as a pale-brown oil. To a solution of 3-nitroaniline (5.73 g, 41.5 mmol) and N,N-dimethylpyridine-4-amine (253 mg, 2.07 mmol) in pyridine (50 mL) was added dropwise a suspension of 3-(cyano-1-methylethyl)benzoyl chloride in pyridine (30 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and to the residue was added saturated aqueous sodium hydrogen carbonate solution (150 mL), and the mixture was extracted with ethyl acetate (200 mL, 50 mL). The combined organic layer was washed with saturated brine (30 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate/hexane mixture to give the title compound (11.46 g, 89%) as a pale-yellow solid.

Provenance & Evidence