Chloride → HCID 49806215, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 8-chloro-9,10-dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride (970 mg, 2.3 mmol) in anhydrous diethyl ether (150 mL) at 0° C. was added a solution of methylmagnesium chloride in tetrahydrofuran (3 M, 15 mL, 45 mmol) dropwise. After stirring at 0° C. for 30 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (50 mL). The mixture was extracted with diethyl ether (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from diethyl ether to afford 9,10-dimethoxy-8,8,13-trimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (80 mg, 9%). LC/MS m/e calcd for C23H25NO4 (M+H)+: 380.46, observed: 380.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (s, 6 H) 2.12 (s, 3 H) 2.63 (t, J=5.18 Hz, 2 H) 3.16 (t, J=5.31 Hz, 2 H) 3.73 (s, 3 H) 3.79 (s, 3 H) 6.01 (s, 2 H) 6.81 (s, 1 H) 6.86-6.93 (m, 2 H) 6.98 (s, 1 H).

Provenance & Evidence