Hydrogen Bromide → HCID 58349496, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-amino-3-chloro-1-methylisoquinoline (460 mg, 2.4 mmol) in HBr (48%, 6 mL) and water (3 mL) at 0° C. was added slowly NaNO2 (165 mg, 2.4 mmol) in water (3 mL). The reaction was stirred at 0° C. for 10 minutes, then the excess NaNO2 was quenched by addition of a small amount of urea. The diazonium solution was then added slowly to a stirred solution of CuBr (411 mg, 2.9 mmol) in HBr (48%, 4 mL) at 75° C. The mixture was stirred for an additional 5 minutes at 75° C., then at room temperature for 18 hours. The mixture was poured onto crushed ice, adjusted to pH 9 with NH4OH, then extracted with EtOAc. The combined organics were washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 10% EtOAc/hexanes to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 8.09 (d, J=6.0 Hz, 1H), 7.98 (d, J=6.0 Hz, 1H); 7.97 (s, 1H), 7.44 (t, J=6.0 Hz, 1H); 2.98 (s, 3H). LC1: 2.68 min, (M+H): 256.

Provenance & Evidence