1969 Volume 42 Issue 10 Pages 2952-2956
The alkaline hydrogen peroxide oxidation of compound A, C17H14O5N2, a base-catalyzed condensation product of o-nitroacetophenone, gave a dehydro compound, C17H12O5N2. The structure of the dehydro compound was deduced from the spectral data of its derivatives to be a (o-nitrobenzoyl)-1-hydroxycarbostyril. The forced hydrogenation of the dehydro compound gave 3-(o-aminobenzoyl)-4-methylcarbostyril, which was synthesized by the condensation of o-aminoacetophenone and ethyl o-nitrobenzoylacetate followed by reduction. Therefore, the dehydro compound proved to be 1-hydroxy-4-methyl-3-(o-nitrobenzoyl)carbostyril. On the other hand, the alkaline hydrogen peroxide oxidation of compound A methyl ether gave o-nitrobenzoic acid and 1-methoxy-3-methyldioxindole along with o-nitroacetophenone. These facts are explained by assuming a transition state which would be controlled by the presence of a hydrogen bonding.
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