The efficient solid-phase synthesis of 3-hydroxy-2,7-disubstituted-6-nitroquinolin-4(1H)-ones using Rink amide resin is described. Synthesis starts from immobilized 4-chloro-5-nitroanthranilic acid which, after the nucleophilic replacement of the chlorine atom with various amines and subsequent esterification with bromoacetophenones, afforded substituted phenacylanthranilates. Their cyclization by heating in sulfuric acid gave corresponding hydroxyquinolinones of excellent purity.
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Křupková et al. (2009) studied this question.
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