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

HRID 1019813Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([CH3:34])(=[O:33])=[O:32])[C:6]([C@@H:12]([N:14]1C(=O)C3C(=CC=CC=3)C1=O)[CH3:13])=[N:7]2.NN>O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([CH3:34])(=[O:33])=[O:32])[C:6]([C@@H:12]([NH2:14])[CH3:13])=[N:7]2

Participants

Conditions

Temperature: 65 °C

Procedure

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).

Workup

customA 5 L three-neck round bottom flask equipped with an overhead stirrer
temperaturethermocouple and reflux condenser with a nitrogen inlet
temperatureto cool to rt overnight

Sources & evidence

ORD record: ord-d4e9ac1d6ae34f529f341d6ddd06521c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716290B2

Reaction notes

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