Hydrochloric Acid → HCID 10263984, compound

Participants

Reaction Conditions

Reaction Steps

3,3-Dicarboxy-4-(indol-3-yl)butanoic acid (10.0 g) was dissolved in freshly distilled quinoline (50 ml) under dry nitrogen and copper powder (1.0 g, 40-80 mesh) was added. The reaction mixture was treated with ultrasound for 0.5 hours and heated to 125° C. for 0.75 hours and 145° C. for 1 hour. The reaction was cooled and poured onto ice, acidified with 5N hydrochloric acid and saturated with sodium sulphate. The mixture was extracted with ethyl acetate (4×100 ml). The combined organic extract was extracted with 5% sodium bicarbonate solution and the combined aqueous extract was poured onto ice, acidified with 5N hydrochloric acid, saturated with sodium sulphate and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and evaporated. The resulting oil was taken up into 1,2 dichloroethane and heated and scratched to induce crystallisation. Filtration gave the title compound as white crystals, mp 144°-145° C.; found: C, 62.93; H, 5.48; N 5.62; C13H13NO4 requires C, 63.15; H, 5.30; N, 5.67%

Provenance & Evidence