The precursor compound of aniline and 10 ml of 6M HCl were placed in a 200 ml beaker, the resulting suspension was heated for 5 min (heat gun), a solution of NaNO2 (393 mg, 5.7 mmol) in 3 ml of water was added dropwise to the reaction mixture at -5 C, the resulting clarified solution was carefully poured into a solution of NaI (2.43 g, 16.2 mmol) in 20 ml of water. The resulting clarified solution was carefully poured into a solution of NaI (2.43 g, 16.2 mmol) in 20 ml of water and the reaction mixture was stirred at room temperature for 10 h. The reaction mixture was extracted with CH2Cl2 and the combined organic layers were washed with 10% NaHSO3 solution, 2M NaOH solution and brine. The combined organic layer was dried with Na2SO4 and the combined organic layer was concentrated.
