Hydrazine hydrate (1:1) → 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

Participants

Reaction Conditions

Reaction Steps

In a 100 mL flask, 2-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl) isoindoline-1,3-dione (2.50 g, 5.08 mmol) was diluted with methanol (25 mL). Hydrazine hydrate (0.740 mL, 15.2 mmol) was added and the reaction mixture was heated to 70° C. and stirred for 3 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane and washed with sodium hydroxide (1 N). The aqueous layer was further extracted with dichloromethane. The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash column chromatography using 50% ethyl acetate/petroleum ether as eluent to afford the title compound as white solid (1.60 g, 88%): mp 143-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.37 (s, 1H), 8.07 (d, J=9.2 Hz, 2H), 8.02 (d, J=8.4 Hz, 2H), 7.62 (d, J=8.4 Hz, 2H), 7.34 (d, J=7.6 Hz, 2H), 2.66 (t, J=7.6 Hz, 2H), 2.56 (t, J=6.8 Hz, 2H), 1.90 (brs, 2H), 1.72-1.62 (m, 2H); ES+ m/z 363 ([M+H]+).

Provenance & Evidence