Ethanol → 3-(1-Amino-2-naphthoyl)benzonitrile

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Reaction Steps

3-(1-nitro-2-naphthoyl)benzonitrile (6.22 g, 20.6 mmol) was dissolved at 65° C. in acetic acid (150 mL), ethanol (150 mL) and water (15 mL). After cooled to room temperature, to the solution was added iron powder (6.67 g, 119 mmol). To the mixture was stirred at 65° C. for 1 hour, and cooled to room temperature. The resultant mixture was added silica gel (100 g), filtered, and the residue was washed with ethyl acetate. The filtrate and washings were combined, washed with a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform), to give the titled compound as a yellow crystal (5.40 g, yield 96%).

Provenance & Evidence