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

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.

Keywords:

• 3-Amino-1H-quinolines
• Synthesis
• Photochemical isomerization

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.