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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 19
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Original Articles

AN IMPROVED METHOD FOR THE SYNTHESIS OF 3-AMINO-1H-QUINOLIN-2-ONE

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Pages 2959-2963 | Received 04 Oct 2001, Published online: 16 Aug 2006
 

ABSTRACT

An efficient method for the synthesis of 3-amino-1H-quinolin-2-one is described. Condensation of o-nitrobenzaldehyde with hippuric acid gave 4-(2-nitrobenzylidene)-2-phenyloxazol-5-one. This compound was reduced to give 4-(2-aminobenzylidene)-2-phenyloxazol-5-one, which upon isomerization with light, cyclization and hydrolysis afforded the desired product.

ACKNOWLEDGMENTS

We are very grateful to Dr. Joseph Muchowski for critical review of the manuscript. We thank Georgina Duarte, Margarita Guzman, Graciela Chávez, Maricela Gutiérrez, Federico García and Rosa I. Del Villar for recording MS, IR, and 1H NMR spectra. This work was supported in part by CONACyT and DGAPA IN204998.

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