Sodium Iodide → 6-Iodoquinoline

Participants

Reaction Conditions

Reaction Steps

Sodium iodide (4.32 g, 28.8 mmol), Copper (I) iodide (137 mg, 0.72 mmol) and N,N′-Dimethyl-cyclohexane-1,2-diamine (0.227 mL, 1.44 mmol) and 6-Bromoquinoline (3 g, 14.4 mmol) in dioxane (15 mL) were charged in a 25 mL microwave tube. The tube was flushed with Nitrogen and sealed with a Teflon septum and Nitrogen was bubbled in the solution for 10 minutes, allowing the gas to escape through a needle. After the removal of the needle, the reaction mixture was stirred at 110° C. for 15 hours. Then, the green suspension was allowed to reach room temperature, poured into ice-water and extracted with dichloromethane. The organic layer was collected, dried (MgSO4), filtered and concentrated in vacuum. The crude mixture was chromatographed over silica gel with CH2Cl2 100% and CH2Cl2/MeOH:95/5 to yield 3.56 g (97%) of 6-Iodoquinoline as a light yellow solid. 1H-NMR (DMSO): δ 8.93 (1H, dd, J=1.5, 4.1 Hz), 8.47 (1H, d, J=2.0 Hz), 8.33 (1H, d, J=8.6 Hz), 8.02 (1H, dd, J=2.0, 8.6 Hz), 7.80 (1H, d, J=8.6 Hz), 7.56 (1H, dd, J=4.1, 8.6 Hz).

Provenance & Evidence