Hydrazine → (S)-1-(5-chloro-3-(2-(methylsulfonyl)phenyl)quinoxalin-2-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

A 5 L three-neck round bottom flask equipped with an overhead stirrer, thermocouple and reflux condenser with a nitrogen inlet was charged with (S)-2-(1-(5-chloro-3-(2-(methylsulfonyl)phenyl)quinoxalin-2-yl)ethyl)isoindoline-1,3-dione (193 g, 392 mmol), water (1351 mL) and hydrazine, 35 wt. % solution in water (711 mL, 785 mmol). The resulting white slurry was vigorously stirred at 65° C. under nitrogen for 6 h and then it was allowed to cool to rt overnight. After this time LC-MS analysis showed complete conversion to the desired product. The white solid was isolated by filtration, washed with water and dried on the glass filter under a stream of nitrogen for 4 h to give (S)-1-(5-chloro-3-(2-(methylsulfonyl)phenyl)quinoxalin-2-yl)ethanamine (129.7 g). Mass Spectrum (ESI) m/z=362.0 (M+1).

Provenance & Evidence