European Journal of Chemistry 2013, 4(1), 53-57 | doi: https://doi.org/10.5155/eurjchem.4.1.53-57.733 | Get rights and content






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An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives


Abdulaziz Alnajjar (1) , Marzouq Alsaiedi (2) , Morsy Ahmed El-Apasery (3,*)

(1) Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, Safat, 70654, Kuwait
(2) Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, Safat, 70654, Kuwait
(3) Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, 12622 Dokki, Giza, Egypt
(*) Corresponding Author

Received: 03 Jan 2013 | Revised: 04 Feb 2013 | Accepted: 05 Feb 2013 | Published: 31 Mar 2013 | Issue Date: March 2013

Abstract


Ethyl 2-amino-3-cyano-4-phenylnicotinates (8), could be readily synthesized via reacting ethyl propiolate with benzylidenemalononitrile in the presence of L-proline as a catalyst and subsequent rearrangement of the so formed 2-aminopyran (7), with acetic acid in the presence of ammonium acetate. A series of 2-amino and 2-hydroxyarylazonicotinates monoazo disperse dyes (12a-c), were prepared in a good yields via condensation of arylhydrazonals (11a-c), with active methylene nitriles. The compound 9 was also characterized by single crystal X-ray diffraction studies. Crystal data for compound 9, C15H18O6 (M = 294.29): hexagonal, space group P65 (no. 170), a = 11.3311(5) Å, c = 19.5375(10) Å, V = 2172.42(18) Å3, Z = 6, T = 296(2) K, μ(MoKα) = 0.879 mm-1, Dcalc = 1.350 g/mm3, 4546 reflections measured (9.02 ≤ 2Θ ≤ 132.96), 2271 unique (Rint = 0.0921) which were used in all calculations. The final R1 was 0.0686 (>2σ(I)) and wR2 was 0.1691 (all data).

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Keywords


Enaminones; Nicotinic acid; Disperse dyes; Arylhydrazonals; Dye intermediates; Arylazonicotinates

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DOI: 10.5155/eurjchem.4.1.53-57.733

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Funding information


The Public Authority for Applied Education and Training (Transform grant TS-07-11) of Kuwait.

Citations

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[1]. Morsy Ahmed El-Apasery, Samar Mohamed Ashkar, Marwan Touma, Mohamed Hilmy Elnagdi
A facile synthesis of some biologically active disperse dyes derived from arylazonicotinates and their application on polyester fabrics
European Journal of Chemistry  4(3), 245, 2013
DOI: 10.5155/eurjchem.4.3.245-249.820
/


[2]. Morsy Ahmed El-Apasery, Fawzia Al-Qalaf, Khaledah Almohammad, Huda Mahmoud
Synthesis of some biologically active monoazo disperse dyes derived from nicotinic acid derivatives under microwave irradiation for dyeing polyester fabrics
European Journal of Chemistry  4(3), 211, 2013
DOI: 10.5155/eurjchem.4.3.211-215.783
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[3]. Saleh Mohammed Al-Mousawi, Morsy Ahmed El-Apasery, Mohamed Hilmy Elnagdi
Arylazoazines and arylazoazoles as interesting disperse dyes: Recent developments with emphasis on our contribution laboratory outcomes
European Journal of Chemistry  5(1), 192, 2014
DOI: 10.5155/eurjchem.5.1.192-200.883
/


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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Alnajjar, A.; Alsaiedi, M.; El-Apasery, M. Eur. J. Chem. 2013, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733
Alnajjar, A.; Alsaiedi, M.; El-Apasery, M. An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives. Eur. J. Chem. 2013, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733
Alnajjar, A., Alsaiedi, M., & El-Apasery, M. (2013). An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives. European Journal of Chemistry, 4(1), 53-57. doi:10.5155/eurjchem.4.1.53-57.733
Alnajjar, Abdulaziz, Marzouq Alsaiedi, & Morsy Ahmed El-Apasery. "An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives." European Journal of Chemistry [Online], 4.1 (2013): 53-57. Web. 10 Apr. 2020
Alnajjar, Abdulaziz, Alsaiedi, Marzouq, AND El-Apasery, Morsy. "An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives" European Journal of Chemistry [Online], Volume 4 Number 1 (31 March 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.1.53-57.733

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