2-(Aminomethyl)-4-bromoaniline

39263-32-6

771583-12-1

The general procedure for the synthesis of 2-aminomethyl-4-bromoaniline from 2-amino-5-bromobenzonitrile is as follows: 5.9 g (0.030 mol, molecular weight 196) of 2-amino-5-bromobenzonitrile was added to a 500 ml three-necked flask, followed by the addition of 45 ml of anhydrous tetrahydrofuran with stirring and cooling to 0 °C. A borane tetrahydrofuran solution (1 M concentration) was added slowly and dropwise to the reaction flask at 0 °C under nitrogen protection and continuous stirring. The reaction mixture was stirred at room temperature for three days. Upon completion, the reaction system was cooled to 0 °C, 20 mL of anhydrous ethanol was added and dry HCl gas was passed to saturation. Subsequently, the reaction solution was concentrated, cooled to 25 °C and 30 ml of isopropyl ether was added to precipitate the product. Under cooling and nitrogen protection, the solid product was transferred to 50 mL of ammonia, stirred, and extracted with ethyl acetate. The organic phases were combined and the solvent evaporated to give the solid product. After drying, 5.4 g of 2-aminomethyl-4-bromoaniline (molecular weight 200) was obtained in 89.6% yield.