Hydrazine hydrate (1:1) → 3-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile

Participants

Reaction Steps

3-Chloro-5-({2-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}oxy)benzonitrile (1.0 g, 2.3 mmol) was dissolved in methanol (25 mL) and hydrazine monohydrate (0.3 mL, 5.9 mmol) was added. The reaction was stirred for 4 h. Additional hydrazine monohydrate (0.3 mL, 5.9 mmol) was added and stirred overnight. The solvent was evaporated and the crude product was purified by column chromatography (hexane/EtOAc) to afford the title compound (0.5 g, 72%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.77 (t, 1H), 7.53 (d, 1H), 7.40 (dd, 1H), 7.32 (t, 1H), 7.19-7.29 (m, 2H), 3.68 (s, 2H), 1.89 (br. s., 2H). MS: m/z 292.9 (M+1).

Provenance & Evidence