A Reported New Synthesis of Lysergic Acid Yields Only The Derailment Product: Methyl 5-Methoxy-4,5-dihydroindolo[4,3-f,g]quinoline-9-carboxylate

The treatment of ethyl 6-formy1-5-(1H-Indol-411)pyridine-3-carboxylate (2) with NaOMe or NaOH in methanol solution at room temperature under the reported reaction conditions afforded solely product 4 in 80% yield, rather than anticipated product 3.