Hydrazine hydrate (1:1) → 1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

2-(1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione (220 mg, 532 μmol) was added to EtOH. To the resulting slurry was added hydrazine hydrate (133 μl, 2658 μmol) and the mixture was heated in an oil bath at 80° C. for 3 h. The reaction mixture was cooled to room temperature, filtered, and rinsed with EtOH (˜10 mL). The filtrate was acidified with 1.0 N HCl (˜5 mL) and concentrated on the rotavap to remove ethanol. A minor amount of solid precipitated and was removed by filtration. The filtrate was neutralized with solid sodium carbonate and extracted (2×) with DCM:IPA (4:1). The organic extracts were dried with sodium sulfate, filtered and concentrated to obtain 103 mg (68%) of a solid/film. LC-MS (+esi, M+H+=284.0). 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 1.42 (d, J=6.65 Hz, 3 H) 4.71 (q, J=6.65 Hz, 1 H) 7.38-7.42 (m, 1 H) 7.60-7.68 (m, 2 H) 7.88-7.97 (m, 2 H) 8.02 (dq, J=7.78, 0.80 Hz, 1 H) 8.68-8.71 (m, 1 H) 8.82 (t, J=0.78 Hz, 1 H). LC-MS (+esi, M+H+=284.0).

Provenance & Evidence