Sodium borohydride → HCID 58349459, compound

Participants

Reaction Steps

To a solution of 3-chloro-1-methyl-5-nitroisoquinoline (2.0 g, 9.0 mmol) in dioxane (48 mL) and MeOH (10 mL) was added nickel (11) chloride hydrate (66 mg, 0.4 mmol), followed by sodium borohydride (0.7 g, 18 mmol). After stirring for two hours, the mixture was quenched by the addition of water (30 mL). The mixture was extracted with EtOAc, then the combined organics were washed with 10% NH4OH (aq) then saturated NaCl (aq). The organics were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 20% EtOAc/hexanes to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 7.55 (s, 1H), 7.53 (d, J=8.5 Hz, 1H); 7.39 (t, J=8.5 Hz, 1H); 6.96 (d, J=8.0 Hz, 1H); 2.98 (s, 3H).

Provenance & Evidence