Indole → HCID 57120626, compound

Participants

Reaction Steps

5,10-Dihydro-2,8-dimethoxy-1,3-dimethylindeno[1,2-b]indole (1.04 g, 3.55 mmol) was dissolved in trifluoroacetic acid (5 cm3) and triethylsilane (0.6 cm3) added with vigorous stirring. Stirring was continued for 4 hours, and the reaction worked up incomplete due to the appearance by t.l.c. of impurities. The solution was poured into water, stirred, and brought to pH 7.0 with solid sodium bicarbonate. The organic material was extracted into DCM, which was washed with sodium bicarbonate solution, and filtered through phase separating filter paper. The product and starting material were separated by column chromatography eluting with 20% EtOAc/60°-80° petrol to yield starting indole (0.06 g, 6%) and a colourless solid. Yield: 0.57 g, 58% .M.p. 149-50° C. (from EtOAc/petrol). 1H NMR (CDCl3) δ: 6.99 (1H, s), 6.79 (1H, m), 6.57 (2H, m), 5.18 (1H, d, J=8.5 Hz), 4.18 (1H, dd(br)), 3.74 (3H, s), 3.65 (3H, s), 3.35 (1H, dd, 3J=8.4 Hz), 3.06 (1H, d(d)), 2.25 (3H, s), 2.15 (3H, s).

Provenance & Evidence