title: 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.
abstract: The treatment of ethyl 6-formyl-5-(1H-indol-4-yl)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.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: Markondaiah
authors.initials: M
authors.lastname: Bekkam
authors.forename: Huaping
authors.initials: H
authors.lastname: Mo
authors.forename: David E
authors.initials: DE
authors.lastname: Nichols
mesh_terms: D007211:Indoles / Q000737:chemistry*; D008237:Lysergic Acid / Q000138:chemical synthesis*; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*
chemical_list: D007211:Indoles; D011804:Quinolines; C571264:methyl 5-methoxy-4,5-dihydroindolo(4,3-f,g)quinoline-9-carboxylate; D008237:Lysergic Acid