2-Amino-5-(1-methylethyl)benzonitrile

51605-97-1

544-92-3

549488-76-8

General procedure for the synthesis of 2-amino-5-(1-methylethyl)benzonitrile from 2-bromo-4-isopropylaniline and cuprous cyanide (I): a mixture of cuprous cyanide (I) (2.5 g, 28.02 mmol) and 2-bromo-4-isopropylaniline (5.0 g, 23.35 mmol) was heated in 1-methyl-2-pyrrolidinone (20 mL) to 195°C for for 4 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 mL) to give a dark solution. It was washed twice sequentially with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride solution (brine) and twice with water. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The product was purified by fast column chromatography with hexane as the starting eluent, and the gradient was increased to 20% ethyl acetate/80% hexane to give the orange oily product 2-amino-5-(1-methylethyl)benzonitrile (3.31 g, 20.66 mmol, 88% yield). Mass spectrum (m/z): 161 (M + 1).