Toward the synthesis of 6-hydroxyquinoline starting from glycerol via improved microwave-assisted modified Skraup reaction

Hanen Saggadi (1, 2) , Denis Luart (1) , Nicolas Thiebault (1) , Isabelle Polaert (2) , Lionel Estel (2) , Christophe Len (1)

1 TIMR - Transformation Intégrée de la Matière Renouvelable
2 LSPC - Laboratoire de Sécurité des Procédés Chimiques

An efficient and modified Skraup reaction and Bamberger rearrangement in neat water were developed using nitrobenzene and an inexpensive, abundant and environmentally-friendly glycerol under microwave irradiation conditions was furnish regioselectively to the 6-hydroxyquinoline. The target compound was obtained in 77% yield via efficient domino reaction with a “one pot eleven steps”.

Keywords: Glycerol; Skraup; Bamberger; Aqueous catalysis; 6-hydroxyquinoline; Microwaves; Domino reaction

Domains: Engineering Sciences [physics]; Chemical and Process Engineering

Hanen Saggadi, Denis Luart, Nicolas Thiebault, Isabelle Polaert, Lionel Estel, et al.. Toward the synthesis of 6-hydroxyquinoline starting from glycerol via improved microwave-assisted modified Skraup reaction. Catalysis Communications, 2014, 44, pp.15-18. ⟨10.1016/j.catcom.2013.07.029⟩. ⟨hal-02409886⟩