Ethanol → HCID 19962045, compound

Participants

Reaction Steps

To a solution of 5-[(4-methy-5-nitroindol-3-yl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione (1.009 g, 3.04 mmol) in a mixture of pyridine (18 mL) and absolute ethanol (2 mL) was added 0.05 g of copper powder and the mixture was heated to reflux under Ar for 2 h. The cooled mixture was filtered and the filtrate was evaporated in vacuo to give a viscous brown oil. This material was taken up in ethyl acetate and the solution was washed (1N HCl, saturated aqueous NH4Cl, brine), dried (Na2SO4) and evaporated to give a yellow solid. Trituration with ether gave 423 mg of the title compound as a tan solid. An additional 166 mg of the product could be recovered by evaporation of the supernatant and retrituration with ether. Total yield=671 mg (80%). An analytical sample was crystallized from ethyl acetate-hexane to give tan crystals, mp 105°-106° C.: IR (KBr) 3340, 1717, 1517, 1335 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.47 (br s, 1H), 7.63 (d, J=9.0 Hz, 1H), 7.30 (d, J=8.6 Hz, 1H), 7.28 (s, 1H), 4.06 (q, J=7.1 Hz, 2H), 3.18 (t, J=7.1 Hz, 2H), 2.77 (s, 3H), 2.68 (m, 2H), 1.16 (t, J=7.1 Hz, 3H). Anal. Calcd for C14H16N2O4 : C, 60.86; H, 5.84: N, 10.14. Found: C, 60.76; H, 5.74; N, 10.00.

Provenance & Evidence