Date of Award
Master of Science (MS)
Robert L. Dressler
This research involved the preparation of 3,4-dihydrocarbostyril by homolytic aromatic substitution using N-bromohydrocinnamamide. 3,4-Dihydrocarbostyril has been prepared in several different ways. It was synthesized in 1937 by the Schmidt reaction using 1-indanone and hydrazoic acid in sulfuric acid-benzene solution. More recently (1975) it was prepared by the reaction of o-chlorobenzaldehyde with 2-alkyl-4, 4-dimethyl-2-oxazoline followed by the elimination of methallylchloride. In this research cyclization, starting with N-bromohydrocinnamamide was investigated by the use of an oxidation-reduction reaction employing ferrous sulfate solution in concentrated sulfuric acid, and also by the action of silver nitrate with acetonitrile as the solvent. Each procedure was used in an attempt to form an activated intermediate which might attack the ortho position of the aromatic ring. Both reactions gave unsatisfactory results. When N-bromohydrocinnamamide was irradiated with ultraviolet light from a 250-W medium pressure mercury arc lamp for forty minutes under dry conditions, cyclization occurred to give 3,4 -dihydrocarbostyril. The identity of the product obtained was confirmed by infrared, nuclear magnetic resonance, and mass spectroscopy.
Copyright 1978 Issam Khoury
Khoury, Issam, "The Preparation of 3, 4-Dihydrocarbostyril by Photochemical Cyclization" (1978). Master's Theses. 1709.