Potassium Iodide → HCID 67603160, compound

Participants

Reaction Steps

At 0°-5° C., a solution of sodium nitrite (0.759 g) in water (5 mL) was added into a suspension of the amine 8 in 2.5 mL of concentrated sulfuric acid and 10 mL of water. After stirring for 15 minutes, a solution of potassium iodide (1.826 g) in 3 mL of water was added slowly. The cloudy, orange-purple solution was stirred at room temperature for 1 hour. The reaction mixture was diluted with water (50 mL) and extracted with with ether (2×100 mL). The etheral extracts were washed with aqueous sodium carbonate solution and water. Removal of solvent and flash chromatography of the residue afforded the iodide 17. 1H NMR (200 MHz, CDCl3) 4.00 (s, 2H), 7.27 (d d, 1H), 7.48 (d d, 1H), 8.13 (s, 1H); MS (EI, m/e, relative intensity %) 244 (M+., 12), 216 (M+. -CO, 7.8), 89 (216 (M+. -CO -.I, 40).

Provenance & Evidence