Ethanol → Dichloromethane methanol ammonium hydroxide

To a suspension of 2-(1-(5-chloro-2-(3-fluorophenyl)quinolin-3-yl)ethyl)-isoindoline-1,3-dione (1.1115 g, 2.580 mmol) in ethanol (51.59 mL, 2.580 mmol) was added hydrazine, anhydrous (0.8097 mL, 25.80 mmol), and the mixture was stirred under reflux. After 1 h, the mixture was cooled to room temperature. The mixture was diluted with CH2Cl2 (50 mL), filtered to removed the precipitated byproduct, and washed the filtered solid with CH2Cl2 (50 mL). The filtrate containing the desired product was concentrated under reduced pressure. The residue was purified by column chromatography on a 80 g of Redi-Sep™ column using 0% to 100% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 25 min, and then 100% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) for 4 min as eluent to give 1-(5-chloro-2-(3-fluorophenyl)quinolin-3-yl)ethanamine as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.87 (1 H, s), 7.97-8.02 (1 H, m), 7.78-7.82 (1 H, m), 7.73 (1 H, dd, J=8.4, 7.6 Hz), 7.52-7.61 (1 H, m), 7.41-7.50 (2 H, m), 7.31-7.39 (1 H, m), 4.29 (1 H, q, J=6.7 Hz), 2.10 (2 H, br. s.), 1.19 (3 H, d, J=6.7 Hz); LC-MS (ESI) m/z 301.1 [M+H]+.