Studies on the Doebner-Miller, Skraup, and Related Reactions. II. Preparation and Cyclization of 4-(2'-Nitroanilino)-3-methylbutan-2-one
- 1 January 1963
- journal article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 16 (5) , 828-832
- https://doi.org/10.1071/ch9630828
Abstract
The intermediate adduct (e.g. III) formed in Skraup and Doebner-Miller reactions has the nature of a Mannich base. It has now been prepared from o-nitroaniline, formaldehyde, and methyl ethyl ketone by the Mannich reaction. It has been cyclized to 3,4-dimethyl-8-nitroquinoline under acidic oxidizing conditions; but it is not cyclized by neutral oxidants, nor by non-oxidizing acids or Lewis acids.Keywords
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