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

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-methylaniline (2.00 g, 10.8 mmol) was dissolved in conc. HCl (10 mL) and heated to 80° C. for 30 minutes. The reaction was then cooled to 5° C. and a solution of NaNO2 (781 mg, 10.8 mmol) in water (4 mL) was added over 10 minutes. The resulting mixture was stirred at 5° C. for 30 minutes before addition of SnCl2 (15.3 g, 80.6 mmol) in conc. HCl (8 mL) over 10 minutes. The mixture was stirred at room temperature for 45 minutes before addition of 50% aqueous NaOH. The resulting precipitate was isolated by filtration and the filtrate was extracted with CH2Cl2. The combined organic phases were dried over MgSO4, filtered and concentrated to provide (4-bromo-2-methylphenyl)hydrazine (1.08 g, 50%).

Provenance & Evidence