3-Iodoaniline → (3-Iodophenyl)hydrazine

Participants

Reaction Steps

To a stirred suspension of 3-iodoaniline (2 g, 9.13 mmol) in 37% hydrochloric acid (11 mL) at 0° C. was added a cold solution of sodium nitrite (0.66 g, 9.59 mmol) in water (3.2 mL). The resulting suspension was allowed to stir for 40 min. Then, a cold solution of tin(II) chloride dihydrate (6.18 g, 27.4 mmol) in 37% hydrochloric acid (4.3 mL) was added to the reaction mixture and stirred for another 40 min. The flask was then placed in the refrigerator for 12 h. The precipitate was isolated by filtration and washed with ice-cold brine (25 mL) followed by 2:1 petroleum ether/ether (25 mL) solution. The light pink solid was dried under vacuum for 2 h to give the title compound 61 (3.63 g, 94% yield) as the SnCl2 complex. LRMS (ESI): calc. 234.0; found 235.0 (MH)+ (compound 61 as the free hydrazine was previously reported in Recueil des Travaux Chimiques des Pays-Bas (1961), 80 1348-56).

Provenance & Evidence