4-Ethylphenylhydrazine hydrochloride

589-16-2

53661-18-0

The general procedure for the synthesis of 4-ethylphenylhydrazine hydrochloride from 4-ethylaniline is as follows: 150 mL of deionized water and 160 mL of 12 N hydrochloric acid were added to a reaction flask containing 24.2 g (0.2 mol) of 4-ethylaniline. After cooling the reaction mixture to 0°C, 14 g (0.2 mol) of sodium nitrite solution dissolved in 140 mL of water was added slowly and dropwise. The reaction temperature was maintained at 0 °C and after 1 h, 112 g (0.496 mol) of stannous chloride dihydrate solution pre-dissolved in 90 mL of 12 N hydrochloric acid was added to the reaction mixture, controlling the temperature of the reaction not to exceed 10 °C during the addition process. After the addition, the reaction was continued with stirring at 10 °C for 1.5 h. The reaction mixture was cooled to 0 °C and then filtered. Upon completion of the reaction, the reaction mixture was filtered and the brown solid product was collected with a measured melting point of 198°C and 95% yield.