The three isomeric ring monochlorinated derivatives of 3-amino-5-hydroxybenzoic acid (1), required for studies of the biosynthesis and synthesis of several important classes of antibiotics, are prepared from methyl 3-amino-5-hydroxybenzoate (5). N-Chlorosuccinimide selectively monochlorinates the 2- and 6-positions of this substrate, whilst perchlorination followed by hydrolysis and regiospecific protodechlorination at the 2- and 6-positions affords the 4-chloro acid.

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Im Rahmen von biosynthetischen Studien werden bei der versuchten Darstellung der Monochlor‐Derivate (lb)‐(Id) der natürlichen Aminosäure (Ia) die im Formelschema skizzierten Reaktionen durchgeführt.