T. Reddy, Desireddy Neha Reddy, B. K. Reddy
2018
Citations
0
Influential Citations
3
Citations
Journal
Asian Journal of Chemistry
Abstract
7-Hydroxyquinolin-2(1H)-one have always been of interest to medicinal chemists and can be found in antipsychotic drug such as brexpiprazole. REXULTI (brexpiprazole) is a serotonindopamine activity modulator (SDAM) for the treatment of schizophrenia and is used as adjunctive therapy to antidepressants for the treatment of major depressive disorder [1,2]. One of the classical synthesis of 7-hydroxyquinolin-2(1H)one starts from commercially available m-anisidine reacting with cinnamoyl chloride to give 3-methoxy cinnamaldehyde followed by cyclization with aluminium chloride [3,4]. Another method starting from 7-hydroxyquinoline would be oxidized to offered 7-hydroxyquinoline-1-oxide, further reaction with acetic anhydride followed by saponification with aqueous NaOH solution to obtain 7-hydroxyquinoloine-2(1H)-one [5-9]. El-Aal and Koraierm [10] reported the synthesis of 7-hydroxyquinolin2(1H)-one with 7-hydroxy-4-methyl coumarin in presence of ammonium acetate and acetic acid. However above mentioned methods have the disadvantages such as high reaction temperature, more by-product formation, usage of hazardous chemicals in the reaction and low yielding. Therefore, these drawbacks motivated us to consider some alternative approaches to synthesize 7-hydroxyquinolin-2(1H)-one (1). Herein, we present 2,3dichloro-5,6-dicyano-p-benzoquinone (DDQ) mediated oxidation of 7-hydroxy-1,2,3,4-tetrahydro-2-quinolinone (4) to give 7-hydroxyquinolin-2(1H)-one (1). This approach enables us the synthesis of brexpiprazole and its intermediate with increased yield and reasonable reaction time. An Innovative Approach for the Synthesis of 7-Hydroxyquinolin-2(1H)-one: A Key Intermediate of Brexpiprazole