Piperidine → 5-Methoxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

Participants

Reaction Conditions

Reaction Steps

Alternatively, a mixture of 5-methoxyindolin-2-one (0.50 g, 3.1 mmol), 2-acetylpyrrole (0.28 g, 2.4 mmol) and piperidine (0.60 g, 0.6 mmol) was placed in a sealed tube and melted. The reaction vessel was sealed and the mixture was heated to 130° C. overnight. The reaction was then cooled to ambient temperature and dissolved in ethyl acetate (2 mL). Chromatography (SiO2, 15 g) using 2:1 hexane/ethyl acetate afforded 5-methoxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (0.24 g); 1H NMR (400 MHz, DMSO-d6) δ 2.78 (s, 3H), 3.82 (s, 3H), 6.38 (m, 1H), 6.70–6.80 (m, 2H), 6.98 (m, 1H), 7.16 (m, 1H), 7.30 (m, 1H), 7.68 (m, 1H) ppm.

Provenance & Evidence