4-Aminobenzonitrile → N-(4-Cyanophenyl)glycine

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Reaction Steps

54.0 g (0.46 mol) of 4-aminobenzonitrile and 107.2 g (0.92 mol) of sodium chloroacetate were suspended in 730 mL of water, and the resulting mixture was stirred at reflux temperature for 4 hours. After cooling to room temperature, pH was adjusted to 8-9 with sodium bicarbonate. The resulting solution was washed with 2×200 mL of ethyl acetate, and 5M hydrochloric acid was added to the aqueous phase until pH=3. The precipitated solid was isolated by filtration, washed with 100 mL of water and dried to yield 57.1 g of 2-(4-cyanophenylamino)acetic acid as an off-white solid. Yield: 70.9%. Purity (HPLC, method 3): 92.9%.

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