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Paper | Regular issue | Vol 31, No. 3, 1990, pp.555-561
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5288
Synthesis of 7-Amino-1,2,3,4-tetrahydroacridine-9-carboxylic Acid and Its Derivatives. Reductionof Nitro Compounds under Alkaline Conditions

Mohammed T. Shipchandler* and Philip G. Mattingly

*Diagnostics Division, D-93C and D-90U, AP-20, Abbott Laboratories, Abbott Park, IL 60064, U.S.A.


Condensation of 5-nitroisatin (1) with cyclohexanone in the presence of alcoholic potassium hydroxide, unexpectedly, produced 7-amino-1,2,3,4-tetrahydroacridine-9-carboxylic acid (2) instead of 7-nitro derivative. The general nature of this reaction was shown by substituting several cyclic ketones in this reaction. A radical anion intermediate is proposed to explain this unusual noncatalytic reduction.