Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)- → (4-Chloro-2-fluoro-5-propan-2-yloxyphenyl)hydrazine

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 11.0 g (0.054 mole) of 4-chloro-2-fluoro-5-(1-methylethoxy)aniline and 50 mL of concentrated hydrochloric acid was cooled to 0° C. and a solution of 3.7 g (0.054 mole) of sodium nitrite in 15 mL of water was added dropwise. The reaction mixture temperature was not allowed to rise above 6° C. during the addition. Upon completion of addition the reaction mixture stirred at 0° C. for 30 minutes and a solution of 26.8 g (0.12 mole) of stannous chloride in 30 mL of concentrated hydrochloric acid was added dropwise. Upon completion of addition the reaction mixture was stirred at 0° C. for one hour then was filtered to collect a solid precipitate. The solid was slurried in 100 mL of aqueous 25% sodium hydroxide and collected by filtration to give 11.0 g of 4-chloro-2-fluoro-5-(1-methylethoxy)phenylhydrazine.

Provenance & Evidence