Sodium Acetate → HCID 20303921, compound

Participants

Reaction Steps

A mixture of 4-carboxy-7-chlorindole-3-propionic acid (40 g, 0.15 mole), acetic anhydride (320 ml), and anhydrous sodium acetate (3.0 g) is stirred and heated at reflux for 18 hours in the dark. The reaction mixture is cooled and then the solvent is removed under vacuum. The residue is taken up in ethanol (180 ml) and sodium hydroxide 10% (155 ml) is added slowly keeping the temperature below 45° C. After stirring for 1 hour at ambient temperature most of the ethanol is removed in vacuo and the solid that separates is recovered by filtration and dried. The yield of 8-chloro-3,4-dihydrobenz[cd]-indol-5(1H)-one is 9.1 g (30%) melting 175°-180° C. (dec). The pure compound, is crystalized from toluene and melts 185°-187° C. (dec.). ##STR14##

Provenance & Evidence