HCID 54419371, compound → (3-Indolylethylidene)acetamidomalonic acid

Participants

Reaction Steps

The diester (72) (930 mg, 1.92 mmol), palladium hydroxide on carbon (Pearlman's catalyst) (125 mg) and 95% ethanol (110 mL) were placed in a Parr hydrogenation vessel and subjected to a hydrogen pressure of 45 psi at 25° C. for 3 hours (until the uptake of hydrogen ceased). The reaction mixture was filtered through Celite to remove the catalyst, then evaporated to dryness to give the title compound (73) (576 mg, 99%) which was used without further purification. δ H (300 M Hz; D2O), 1.55 (3H, d, J 7 Hz, CH3), 1.99 (3H, S, CH3CO), 4.09 (1H, brd, J 7 Hz, CH,(CH3), 7.12-7.24 (3H, m), 7.49 (1H, d, J 8 Hz, indole 7-H), 7.71 (1H, d, J 8 Hz, indole 4-H).

Provenance & Evidence