Chlorosuccinimide → 5-Bromo-7-chloro-8-quinolinamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-amino-5-bromoquinoline (440 mg, 1.97 mmol) in CH3CN (39 mL) was added N-chlorosuccinimide (250 mg, 1.87 mmol). The mixture was stirred at 75° C. until no further conversion of the starting material was observed by LC/MS and TLC analysis. The mixture was allowed to cool to room temperature then concentrated. The residue was dissolved in EtOAc, then washed with water (2×50 mL) then saturated NaCl (aq) (50 mL). The organic phase was dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 15% EtOAc/hexanes to afford the title compound as a solid: 1H NMR (500 MHz, CDCl3): δ 8.81 (dd, J=1.4, 4.1 Hz, 1H) 8.43 (dd, J=1.4, 8.5 Hz, 1H), 7.71 (s, 1H), 7.51 (dd, J=4.1, 8.5 Hz, 1H); LC6: 4.27 min. (M+H) 259.

Provenance & Evidence