Hydrazine → (2-Chloro-5-iodophenyl)methanamine hydrochloride

Participants

Reaction Steps

Compound 63 (350 mg, 0.88 mmol) was dissolved in dry EtOH (15 mL) and hydrazine (0.1 mL) was added. The stirred mixture was refluxed for 24 h, cooled and the EtOH evaporated. The residue was dissolved in Et2O (3 mL) and treated with HCl/Et2O. The precipitated hydrochloride salt was filtered and triturated with dry Et2O (3×2 mL), obtaining 200 mg of product (yield 75%). 1H NMR (D2O, 300 MHz) δ 7.88 (s, 1H), 7.80 (dd, J=8.4, 1.8 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 4.27 (s, 2H). MS (m/e) (positive FAB) 268.1 (M−Cl)+, m.p. 207-210° C.

Provenance & Evidence