Chlorosuccinimide → 4-Chloroisoquinolin-3-amine

Participants

Reaction Steps

To isoquinolin-3-amine (2.02 g, 14.0 mmol) in methanol (60 mL) was added N-chlorosuccinimide (2.19 g, 16.4 mmol) at room temperature. The reaction was stirred at room temperature for 3 hours, then concentrated in vacuo. The crude material was chromatographed (Biotage: 10-100% ethyl acetate/hexanes) to yield 4-chloroisoquinolin-3-amine (2.1 g, 11.8 mmol, 84% yield) as a solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.86 (s, 1H), 7.93 (d, J=7.6 Hz, 1H), 7.79 (d, J=8.5 Hz, 1H), 7.68 (td, J=6.7, 1.8 Hz, 1H), 7.24-7.35 (m, 1H), 6.32 (br. s., 2H). MS (LC/MS) R.T.=1.50; [M+H]+=178.96.

Provenance & Evidence