Iodine chloride → HCID 49806332, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 9,10-dimethoxy-8,8-dimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (182 mg, 0.5 mmol) in anhydrous dichloromethane (20 mL) at 25° C. was added Iodine monochloride (0.57 g, 3.5 mmol). After stirring in the dark at 25° C. for 72 h, the reaction was washed twice with aqueous 10% sodium thiosulfate solution (2×50 mL) to remove excessive iodine monochloride, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by Waters Automated Flash System (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 12-chloro-9,10-dimethoxy-8,8-dimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (9.6 mg, 4%). LC/MS m/e calcd for C22H22ClNO4 (M+H)+: 400.88, observed: 400.1; 1H NMR (400 MHz, MeOD) δ ppm 2.05 (s, 6 H) 3.14 (m, 2 H) 3.93 (s, 3 H) 4.01 (s, 3 H) 4.23 (m, 2 H) 6.22 (s, 2 H) 7.04 (s, 1 H) 7.32 (s., 1 H) 7.63 (s, 1 H).

Provenance & Evidence