3-Amino-p-cresol → 3-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide

Beteiligte Stoffe

Reaktionsschritte

To a two-layer solution of 3-amino-4-methylphenol (5.92 g, 48.0 mmol) in tetrahydrofuran (40 mL)/1N aqueous sodium hydrogencarbonate solution (54 mL) was added a solution of 3-(1-cyanocyclopropyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 2 hr. Since the reaction mixture showed pH 4-5, sodium hydrogencarbonate (900 mg, 10.7 mmol) was added to adjust the pH to 8-9, and the reaction mixture was further stirred at room temperature for 1 hr. The aqueous layer was separated, and extracted with ethyl acetate (150 mL). The combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained suspension was added ethyl acetate (25 mL)/hexane (50 mL), and the mixture was stirred at room temperature for 20 min. The precipitate was collected by filtration, repeatedly washed with diisopropyl ether/hexane (1:1) and air-dried to give the title compound (12.2 g, 87%) as a pale-yellow powder.

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