Indole → HCID 178467346, compound

Participants

Reaction Steps

To a solution of 2-acetoxymethyl-3,5-diacetyl-4-methylpyrrole (0.200 g) and indole (0.098 g) in dichloroethane (90 cm3) was added Montmorillonite K10 clay (0.30 g). The mixture was stirred and heated at reflux for 80 h. After cooling the clay was removed by filtration and the filtrate concentrated to ca 20 cm3 in vacuo. The crude product was removed by filtration and then chromatographed on silica. Elution with chloroform-methanol (60:1) yielded 0.08 g of the title compound as a yellow solid m.p. 258°-260° C., m/z (EI) 276 (M+) δH ([2H6 ]-DMSO) 2.58 (3H, s, COCH3), 2.88 (3H, s, CH3), 2.92 (3H, s, CH3), 7.05 (1H, m, 8-H), 7.38 (2H, m, 6-H, 7-H), 7.85 (1H, s, 10-H), 8.08(1H, J, 8 Hz, 9-H), 10.6 (1H, s, NH), 11.17 (1H, s, NH). (Found: C, 77.0; H, 5.74; N, 9.76; C18H16N2 O. 0.14 EtOAc requires C, 77.2; H, 5.98; N, 9.70%.)

Provenance & Evidence