• ESMAEIL CHAHARDOLI

      Articles written in Journal of Chemical Sciences

    • Reinvestigating the synthesis of key intermediates in the preparation of zolazepam—I: (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl) (2-fluorophenyl) methanone

      HOSSEIN FAKHRAIAN YASER NAFARI MOHAMMAD JAVAD TAGHIZADEH ESMAEIL CHAHARDOLI

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      The synthesis of (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)(2-fluorophenyl) methanone (IV) asthe key intermediate in the preparation of zolazepam is reconsidered. The previous report for the preparationof this compound consist of acylation of 5-chloro-1,3-dimethylpyrazole (prepared from chlorination of 1,3-dimethyl-5-pyrazolone) by 2-fluorobenzoyl chloride (II). Herein, the preparation of (IV) via chlorination of(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)(2-fluorophenyl) methanone (III) which was prepared by acylationof 1,3-dimethyl-5-pyrazolone (I) by II is investigated. Different aspects of each step (reaction conditions, sideproducts and workup procedure) were considered and the products and side products were characterized via 1H NMR, 13C NMR and GC-MS techniques.

      The synthesis of (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)(2-fluorophenyl) methanone (IV), as the key intermediate in the preparation of zolazepam, via chlorination of (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)(2-fluorophenyl) methanone (III) which was prepared by acylation of 1,3-dimethyl-5-pyrazolone (I) by II is reconsidered. Different aspects of each step (reaction conditions, side products and workup procedure) were considered and the products and side products were characterized via 1H NMR, 13C NMR and GC-MS techniques.

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