Hydrochloric Acid → Dichloromethane methanol ammonium hydroxide

Participants

Reaction Steps

To a suspension of 2-(((S)-1-(8-chloro-2-(2,3-difluorophenyl)quinolin-3-yl)ethyl)-carbamoyl)benzoic acid (0.2515 g, 0.5387 mmol) in ethanol (3.000 mL, 0.5387 mmol) was added 12 N HCl (1.500 mL, 18.00 mmol), and the mixture was stirred under reflux. After 12 h, the mixture was poured into ice water (50 mL). The mixture was neutralized with NaHCO3 and extracted with CH2Cl2 (50 mL×3). The combined organic layers were washed with brine (50 mL×3), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on a 40 g of Redi-Sep™ column using 0% to 50% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 14 min and then 50% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 for 5 min as eluent to give (1S)-1-(8-chloro-2-(2,3-difluorophenyl)quinolin-3-yl)ethanamine as a light green syrup: LC-MS (ESI) m/z 319.1 [M4-1-1]+.

Provenance & Evidence