3-CHLORO-O-ANISIDINE 97

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3-chloro-2-methoxyaniline (5 g, 31.7 mmol, 1.0 eq) in conc. HCl (25 mL) was added a solution of NaNO2 (3.28 g, 47.55 mmol, 1.5 eq.) in water (5 mL) dropwise at −5 to 0° C. until the reaction mixture formed a clear solution. The reaction mixture was added drop wise to a stirred solution of SnCl2 (13.24 g, 69.74 mmol, 2.2 eq) in conc. HCl (50 mL) at −5° C. for 30 min. A solid precipitate obtained was filtered out and washed with excess of ice cold water to get (3-chloro-2-methoxyphenyl)hydrazine (6.049 g, 94%, brown solid; TLC system: EtOAc/PE (3:7) Rf: 0.4). formed a clear solution A solid precipitate obtained was filtered out washed with excess of ice cold water