Hydrochloric Acid → 7,8,9-Trimethoxy-2,3-methylenedioxy-11H-indeno[1,2-c]isoquinoline Hydrochloride

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Reaction Conditions

Reaction Steps

Amine 12b (2.28 g, 9.52 mmol) and 3,4,5-trimethoxybenzaldehyde (10c, 3.77 g, 19.2 mmol) were reacted in trifluoracetic acid (25 mL) with stirring at 100° C. for 3 h. The reaction mixture was cooled and hydrochloric acid (2 M in ether, 10 mL) and ether (200 mL) were added. The precipitate was isolated and dissolved in methanol-water-acetone 1:1:1 (250 mL) and NH4OH was used to bring the mixture to a basic pH. The mixture was extracted with chloroform (350 mL). The organic layer was washed with brine (200 mL), dried (Na2SO4) and concentrated. The residue was dissolved in chloroform (60 mL) and hydrochloric acid (2 M in dry ether, 10 mL) was added. The precipitate was collected and washed with hot methanol (10 mL) and ether 20 (mL) to provide a yellow hygroscopic solid (1.65 g, 45%), mp 257-259° C. 1H NMR (300 MHz, CD3OD) δ 9.04 (s, 1H), 7.63 (s, 1H), 7.51 (s, 1H), 7.18 (s, 1H), 6.32 (s, 2H), 4.28 (3H), 4.25 (2H), 3.98 (3H), 3.90 (s, 3H); low resolution ESIMS m/z (rel intensity) 352 (MH+, 100). Anal. Calcd for C20H18NO5Cl(H2O)1.9: C, 56.92; H, 5.21; N, 3.32. Found: C, 56.92; H, 5.02; N, 3.29.

Provenance & Evidence