Triethylamine → 7-Chloroisoquinolin-3-amine

Participants

Reaction Steps

7-Chloroisoquinoline-3-carboxylic acid (3.1 g, 14 mmol) was dissolved in 6 N HCl (50 mL), and the mixture was heated under reflux for 4 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was dissolved in tert-butanol (100 mL), and triethylamine (2.8 g, 28 mmol) and diphenylphosphoryl azide (5.6 mL, 26 mmol) were added. The mixture was heated under reflux overnight. After cooled to room temperature, the solvent was distilled off under reduced pressure. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/1) and afforded the title compound (500 mg, 20% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 8.62 (s, 1H), 7.66 (d, J=9 Hz, 1H), 6.86 (d, J=2.4, 1H), 6.75 (dd, J=2.4 and 9 Hz, 1H), 6.52 (s, 1H), 5.83 (s, 1H), 3.83 (s, 3H); MS: m/z 174.1 (M+H+).

Provenance & Evidence