3-Chloroaniline → (3-Chlorophenyl)hydrazine

Participants

Reaction Steps

3-chloroaniline (K-IV) (1 equivalent, 50 g) was dissolved at −5 to 0° C. in concentrated HCl (300 mL) and stirred for 10 min. A mixture of NaNO2 (1.2 equivalents, 32.4 g), water (30 mL), SnCl2.2H2O (2.2 equivalents, 70.6 g) and concentrated HCl (100 mL) was added dropwise over a period of 3 h while maintaining the temperature. After stirring for a further 2 h at −5 to 0° C., the reaction mixture was set to pH 9 using NaOH solution and extracted with ethyl acetate (250 mL). The combined organic phases were dried over magnesium sulfate and the solvent was removed under vacuum. The purification by column chromatography (silica gel: 100-200 mesh, eluent: 8% ethyl acetate/n-hexane) produced 40 g (72%) of (3-chlorophenyl)hydrazine (K-IV) as a brown oil.

Provenance & Evidence