2,3-Dichloroaniline → (2,3-Dichlorophenyl)hydrazine

Participants

Reaction Steps

To a stirred suspension of 2,3-dichloroaniline (35 g, 216.02 mmol, 1.0 eq.) in conc. HCl (150 mL) was added a solution of NaNO2 (17.9 g, 259.22 mmol, 1.2 eq.) in water (50 mL) dropwise at −5 to 0° C. until the reaction mixture formed a clear solution. The reaction mixture was added dropwise to a stirred solution of SnCl2 (90.1 g, 475.24 mmol, 2.2 eq.) in conc. HCl (300 mL) at −5° C. for 30 min. A solid precipitate obtained was filtered out and washed with excess of ice cold water to get (2,3-dichlorophenyl)hydrazine (45.8 g, 98%, pale yellow solid; TLC system: EtOAc/PE (3:7) Rf: 0.55).

Provenance & Evidence