Synthesis of ammonium-alkylaniline dihalides using the Green catalyst Maghnite-H+and characterization

Dj. Chikh Djaoutsi, R. Meghabar


Abstract:The overall objective of this study is to synthesize ammonium salts by adding  dihalogenated compounds such as dibromides and dichlorides to aniline  using the green catalyst "Maghnite-H+", a new non-toxic catalyst.

The important part of this work consisted of carrying out the formation of these ammonium salts under suitable conditions without solvent, at room temperature, for different durations and using several catalyst contents.

The effect of time and amount of catalyst on the yield of the addition reactions was studied. All the synthesized products were characterized by IR spectroscopy,1H-NMR and 13C-NMR.


Full Text:



Pan, Y.Y.; Wu, Y.N.; Chen, Z.Z.; Hao, W.J.; Li, G.; Tu, S.J.; Jiang, B.. Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization. Journal of Organic Chemistry, 80, 11, (2015), 5764-5770

Wang, M.R.; Deng, L.; Liu, G.C.; Wen, L.; Wang, J.G.; Huang, K.B.; Tang, H.T.;Pan, Y.M. Porous Organic Polymer-Derived Nanopalladium Catalysts for Chemoselective Synthesis of Antitumor Benzofuro[2,3-b]pyrazine from 2-Bromophenol and Isonitriles.Organic Letters. 21, 13, (2019), 4929-4932

Haelsig, K.T.; Xuan, J.; Maimone, T.J.Total Synthesis of (−)-Curvulamine. Journal of the American Chemical Society .142, 3, , (2020), 1206-1210

Xu, P.; Wang, F.; Wei, T.Q.; Yin, L.; Wang, S.Y.; Wang, S.Y.;Ji, S.J.Organic. Letters. 19, 17, (2017), 4484-4487

Zarei, M.; Abadi, H.; Mohebat, R.; Mosslemin, M.H. A Novel Eco-Friendly Catalyst- and Solvent-Free Four-Component Synthesis of Benzo[ a ]furo[2,3- c ]phenazines under Microwave Conditions. Polycyclic Aromatic Compounds. 40 (1), (2020), 159-165

Zhu, A.; ,Zhan, W.; Liang, Z.; Yoon, Y. Yang, H.; Grossniklaus, H.E.; Xu, J.; Rojas, M.; Lockwood, M.; Snyder, J.P.; Liotta, D.C. Dipyrimidine amines: a novel class of chemokine receptor type 4 antagonists with high specificity. Journal of Medicinal Chemistry, 53(24), (2010):8556-8568

Bi, W.; Bi, Y.; Li, P.; Bi, L. Indole Alkaloid Derivative B, a Novel Bifunctional Agent That Mitigates 5-Fluorouracil-Induced Cardiotoxicity. American Chemical Society (2018)

Monopoli, A.; Cotugno, P.; Cortese, M.; Calvano, C.D.; Cimie, F and Nacci, A. Selective N-alkylation of

Arylamines with Alkyl Chloride in Ionic Liquids: Scope and Applications. European Journal of Organic Chemistry , (2012)

Bilek,S.; MehmetYılmaz, F.; Özkan, G. The effects of industrial production on black carrot concentrate quality and encapsulation of anthocyanins in whey protein hydrogels. Food and Bioproducts Processing.

Volume 102, (2017) 72-80

Brielles, C.; Harnett, J.J.; Doris, E. Diethylzinc/CuII-mediated alkylation of aromatic amines and related compounds. Tetrahedron Letters. 42, (2001) 8301.

Liu, H.F.; Zhu, T.H.; Xu, P.; Wang, S.Y.; Ji, S.J. I 2 /CHP mediated [1 + 1 + 1 + 1] cyclization of aromatic isocyanides with amines to construct 1,3-diazetidine-2,4-diimine derivatives.Organicand Biomolecular Chemistry, 15 (41) , (2017) 8738-8742.

Sarno, M.; Cirillo, C.; Iuliano, M.Self‐Suspended

Nanoparticles for N‐Alkylation Reactions: A New Concept for Catalysis, ChemistryOpen .Volume 8,

Issue 4, (2019) 399-550

Pranab, J.; Das. P.J.;Das, D..Pyridinium based ionic liquids as promoters for a green and selective synthesis of N-monomethylanilines Iranian Journa of Catalysis , (2019)

Zhou, W.; Hu, Z.C.; Huang, F.; Hong, W.; Chen, X. Metal-free hydrophilic D-A conjugated polyelectrolyte dots/g-C3N4 nanosheets heterojunction for efficient and irradiation-stable water-splitting photocatalysis Applied Catalysis B: Environmental Volume 270, (2020)

Blondiaux, E.; Pouessel, J.; Cantat, T. Carbon Dioxide Reduction to Methylamines under Metal-Free Conditions. Angewandte Chemie, 53 (45), (2014), 12186-12190

Tlili, A.; Blondiaux, E.; Frogneux, X.; Cantat, T. Reductive functionalization of CO2 with amines: an entry to formamide, formamidine and methylamine derivatives,Green Chemistry Volume 17 Numéro1 (2015), 157-168

Jacquet, O.; Frogneux, X.; Das, C.; Gomes, N.; Cantat, T. CO2 as a C1-building block for the catalytic methylation of amines,Chemical Science. Volume 4, Numéro 5, (2013), 2127-2131

Stauffe, S.R and Hartwig, J.F. Fluorescence resonance energy transfer (FRET) as a high-throughput assay for coupling reactions. Arylation of amines as a case study,” Journal of the American Chemical Society, 125, 23, (2013) 6977–6985

Kim , K.H.; Lee , C.Y.; Cheon . Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination, The Journal of Organic Chemistry, 80, 12, (2015) 6367-6374

Chun-Young Lee and Cheol-Hong Cheon, Development of Organic Transformations Based on Protodeboronation, Boron Reagents in Synthesis,Chapter 15, (2016) 483-523

Iryna, D.; Alshakova. Dr.; Georgii, I. Selective

Synthesis of Secondary and Tertiary Amines by Reductive N‐Alkylation of Nitriles and N‐Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex.ChemCatChem Volume 11, Issue 21(2019):

Bauke, A.; Nils, M.N. Highly Potent Antibacterial Organometallic Peptide Conjugates. Accounts of Chemical Research 50, 10, (2017) 2510-2518

De Souzai, J.M.; Galaverna, R.; De Souza, A.A.N.; Brocksom, T.J.;.Pastre, J.C.; De Souzai, R.O.M..A and De Oliveira, K.T .Impact of continuous flow chemistry in the synthesis of natural products and active pharmaceuticalingredients Anais da Academia Brasileira de Ciências. 90 (1 Suppl. 2), (2018) 1131-

Cheng, C.; Brookhart, M. Journal of the American Chemical Society. 134, (2012) 11304-11307. Moro, A.; Schmidt, J.; Doussineau, T.;Lapresta-Fernández, A. .Surface-functionalized fluorescent silica nanoparticles for the detection of ATP,

Chemical Communications 47 (21) (2011), 6066-8

Wei, Bi.; Yue, Bi.; Pengfei, Li.; Lanrong, Bi. Indole Alkaloid Derivative B, a Novel Bifunctional Agent That Mitigates 5-Fluorouracil-Induced Cardio–toxicity. American Chemical Society (2018)

Amat, A.; Guignard, G.; Llor, N. Bosch, J. Journal of Organic. 79, (2014) 2792–2802

Niu, D.; Buchwald, S.LBuchwald SL. Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination. . Journal of the American Chemical Society.137, (2015) 9716–9721.

Li, X.; Li, S.; Li, Q.; Dong, X.; Li, Y.; Yu, X.; Xu, Q.Tetrahedron.72, (2016) 264–272

Belbachir, M; Bensaoula , A. Composition and method for catalysis using bentonite .U.S. Patent 7094823. USA . (2006)

Haoue,S.; Derdar, H.; Belbachir, M.; Harrane, A. Polymerization of Ethylene. Glycol Dimethacrylate Using An Algerian Clay as Eco-catalyst (Maghnite-H+ and Maghnite-Na+).Bulletin of Chemical Reaction Engineering and Catalysis. 15(1), (2020) 221-230 •

Derkaoui, S .;Kherroub, D.E.; Belbachir , M, Green synthesis, anionic polymerization of 1, 4-bis (methacryloyl) piperazine using Algerian clay as catalyst.Green Processing and Synthesis, (2019)

Boulaouche,T.;Kherroub, D.E.; Khimeche, K.; Belbachir, M. Green Processing and Synthesis 8(1), (2019) 611-621

Kherroub, D.E.; Belbachir, M.; Lamouri, S. Green Polymerization of Hexadecamethylcyclooctasiloxane Using an Algerian Proton Exchanged Clay Called Maghnite-H+ .Bulletin of Chemical Reaction Engineering et Catalysis, 13, (2018) 36-46.

Kherroub, D.E.; Khodja, M.; Belbachir, M.; Lamouri, S.; Bouhadjar, L .; Boucherdoud, A. Maghnite-H+ as Inorganic Acidic Catalyst in Ring opening Polymerization of Dodecamethylcyclohexa -siloxane Silicon, volume 11, (2019)1165–1


  • There are currently no refbacks.

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License. Copyright UMMB © 2020 University M'hamed Bougara - Boumerdes. Independance AV., Boumerdes, 35000 Algeria, Tel/Fax: +213 24 91 14 98/ +213 2491-29-51