[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH:8]=1)[NH2:7].[N:11]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([NH:7][NH2:11])[CH:8]=1To a stirred suspension of 5-chloro-2-methoxyaniline (20.0 g, 126.98 mmol, 1.0 eq) in conc. HCl (250 mL) was added a solution NaNO2 (10.5 g, 152.38 mmol, 1.2 eq) in water (40 mL) dropwise at −5-0° C. until reaction mixture formed a clear solution. The reaction mixture was added dropwise to a stirred solution of SnCl2 (52.90 g, 279.36 mmol, 2.2 eq) in conc. HCl (250 mL) at −5° C. for 30 min. The solid precipitate obtained was filtered out and washed with excess of ice cold water to get (5-chloro-2-methoxyphenyl)hydrazine (25.3 g, 92%, off-white solid; TLC system: EtOAc/PE (3:7) Rf: 0.6).
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