Sodium Bicarbonate → N-(4-cyano-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide

Beteiligte Stoffe

Reaktionsschritte

To a two-layer solution of 4-amino-2-hydroxybenzonitrile (3.16 g, 23.5 mmol) in tetrahydrofuran (80 mL)/1N aqueous sodium hydrogen carbonate solution (80 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 18 hr. The aqueous layer was separated, and extracted with ethyl acetate (100 mL). The combined organic layer was washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in methanol (300 mL), anhydrous potassium carbonate (3.5 g) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate (300 mL) was added to the obtained residue, and the mixture was washed with water (150 mL) and saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate (50 mL)/hexane (50 mL) to give the title compound (3.10 g, 44%) as a pale-brown powder.

Herkunft & Nachweise