Ethyl Acetate → HCID 10069251, compound

Participants

Reaction Steps

3-(6-cyano-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (9.0 g, 21 mmole) was suspended in ethanol (1.8 L) and treated with tin (II) chloride dihydrate (35 g, 156 mmole). This was mechanically stirred for 16 h at reflux. The reaction was cooled and reduced in volume to 1L. This was poured into a mixture of ethyl acetate (2 L) and saturated sodium bicarbonate solution (1 L) and well mixed. The organic layer was decanted and washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered, evaporated, and then purified by flash column chromatography (ethyl acetate). The product was further purified by crystalization from tetrahydrofuran/hexane to provide 6.5 g of 3-[4-(6-amino-1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1-methyl-1H-indole-6-carbonitrile; mp 255-260° C.

Provenance & Evidence