4-Bromo-2-methylaniline → (4-bromo-2-methylphenyl)hydrazine

Participants

Reaction Conditions

Reaction Steps

4-bromo-2-methylaniline (2.0 g) was dissolved in conc. HCl (10 mL) and heated to 80° C. for 30 minutes. The reaction was cooled to 5° C. and a solution of sodium nitrite (781.0 mg in 4.0 mL of water) was added over 10 minutes. The resulting mixture was then stirred at 5° C. for 30 minutes. A solution of tin(II)chloride (15.3 g in 8 mL of concentrated HCl) was added over 10 minutes, and the resulting solution was stirred at room temperature for 45 minutes. The reaction was made basic with 50% NaOH solution and a white precipitate formed. The solid was filtered and the filtrate extracted with dichloromethane. The organic extract was dried over magnesium sulfate, filtered and concentrated to yield 1.08 g (50%) of 1-(4-bromo-2-methylphenyl)hydrazine as a white solid. LC-MS @ 201.1 (M+1)

Provenance & Evidence