35747-58-1

16588-02-6

35747-58-1

The general procedure for the synthesis of 3-cyano-4-chloroaniline from 2-chloro-5-nitrobenzonitrile was as follows: 2-chloro-5-nitrobenzonitrile (10 g, 54.8 mmol) was heated and refluxed for 1 h in a mixture of isopropanol (125 mL) and concentrated hydrochloric acid (62.5 mL) with stannous chloride dihydrate (56 g, 248.6 mmol). Upon completion of the reaction, the mixture was cooled to room temperature and neutralized with 2N sodium hydroxide solution. Subsequently, the aqueous layer was extracted with dichloromethane, the organic layers were combined and dried with anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to afford 3-cyano-4-chloroaniline (8 g, 96% yield). The product was analyzed by high performance liquid chromatography (HPLC) under the following purity detection conditions: detection wavelength 210-370 nm; retention time (RT) 7.2 min; mobile phase 10 mM ammonium formate buffer (pH 3.5)/acetonitrile + methanol (gradient elution from 85/15 to 5/95) for 10 min, hold for 4 min; chromatography column Xterra TM RP18 (3.5 μm, 150×4.6 mm); mobile phase 1.5 μm, 2.5 μm, 2.5 μm, 2.5 μm, 2.5 μm, 2.5 μm. m, 150×4.6 mm); the flow rate was 1.2 mL/min.