Chloride → HCID 49806218, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 8-chloro-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride (0.2 g, 0.5 mmol) in anhydrous diethyl ether (5 mL) at 0° C. was added a solution of allylmagnesium chloride in tetrahydrofuran (1.3 M, 2.16 mL, 4 mmol) dropwise. After stirring at 0° C. for 30 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (10 mL). The mixture was extracted with diethyl ether (2×50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from diethyl ether to afford 8,8-diallyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (28 mg, 13%). LC/MS m/e calcd for C26H27NO4 (M+H)+: 418.51, observed: 418.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.66-2.78 (m, 4 H) 2.94 (dd, J=15.41, 6.06 Hz, 2 H) 3.26 (t, J=5.43 Hz, 2 H) 3.77 (d, J=10.36 Hz, 6 H) 4.88 (d, J=10.36 Hz, 2 H) 4.98 (d, J=17.43 Hz, 2 H) 5.35 (s, 1 H) 5.66-5.78 (m, J=16.99, 10.29, 7.07, 6.82 Hz, 2 H) 5.98 (s, 2 H) 6.51 (d, J=8.34 Hz, 1 H) 6.72 (s, 1 H) 6.80 (d, J=8.34 Hz, 1 H) 7.15 (s, 1 H).

Provenance & Evidence