CONTRIBUTION OF NMR SPECTROSCOPY, MASS SPECTROMETRY AND X-RAY DIFFRACTOMETRY TECHNIQUES TO THE CHARACTERIZATION OF 2-CHLORO-8-METHYL-3-FORMYLQUINOLINE
Abstract
Quinoline and its analogues have been known to possess diverse pharmacological activities. In the last three decades 2-chloro-8-methyl-3-formylquinoline has been utilized as building blocks for the development of various quinolines fused heteroaryl rings. In this article we report the complete spectral details of 2-chloro-8-methyl-3-formylquinoline. The techniques involved in the characterization of title compounds are various NMR experiments such as HSQC, COSY and HMBC. Molecular weight was determined by FAB-mass spectrometry. The powder XRD study revealed crystal behavior of the title compound.
Keywords:
HSQC, COSY, HMBC, XRD and 2-chloro-8-methyl-3-formylquinolineDOI
https://doi.org/10.25004/IJPSDR.2014.060304References
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2. Bhrigu B, Pathak D, Siddiqui N, Alam MS, Ahsan W. Search for Biological Active Isatins: A Short Review. Internat. J. Pharm. Sci. Drug Res. 2010; 2(4): 229-235.
3. Desai UH, Patwari AH, Maradiya JK, Sathawara MK, Suhagia BN, Rathod IS. RP-HPLC Method for Simultaneous Estimation of Ciprofloxacin and Dexamethasone in Eye/Ear Drops. Internat. J. Pharm. Sci. Drug Res. 2013; 5(2): 62-66
4. Nyerges M, Pintér A, Virányi A, Blaskó G, Tőke L. Synthesis of pyrrolo[3,4-c]quinolines by 1,5-electrocyclisation of non-stabilized azomethine ylides. Tetrahedron. 2005; 61: 8199-8205.
5. Cziaky Z, Szabó Z. Synthesis of 2H-pyrano[2,3-b]quinolines. Part II. Preparation and 1H-NMR investigations of 4-hydroxy-2-methyl-3,4-dihydro-2H-pyrano[2,3-b]quinolines. J. Hetero. Chem. 1995; 32: 755-760.
6. Bawa S, Kumar S. Synthesis of Schiffs bases of 8-methyl-tetrazolo[1,5-a]quinoline as potential anti-inflammatory and antimicrobial agents. Indian J. Chem. 2009; 48B: 142-145.
7. Eswaran S, Adhikari AV, Kumar RA. New 1, 3-oxazolo[4,5-c]quinoline derivatives: Synthesis and evaluation of antibacterial and antituberculosis properties. Euro. J. Med. Chem. 2010; 45: 957–966.
8. Srivastava A, Chandra A, Singh RM. Isothiazolo-fused quinoline analogues : Synthesis of isothizolo[5,4-b]quinoline and their oxidation product, 3[2H]-one-1,1 dioxideisothiazolo[5,4-b]quinoline from 2-chloro-3-formylquinoline. Indian J. Chem. 2007; 46B: 303-307.
9. Amaravathi M, Babu MM, Chandramouli G. Synthesis of meso- tetrakis (2-chloroquinolin-3-yl) porphyrins. Arkivoc. 2007; (i): 148-153.
10. El-Baih FEM, Al-Aqeel SI, El-Sayed OA, Al-Hazimi HM. Synthesis and spectroscopic properties of some pyrimido[4,5-b]quinoline derivatives. J. King Saud. Univ. 2005; 18: 1-17.
11. Fused pyridine and pyrazine derivatives as kinase inhibitors. 2010 WO/2010/092340.
12. Thomas CJ, Rahier NJ, Hecht SM. Camptothecin: Current perspectives. Bioorg. Med. Chem. 2004; 12: 1585–1604.
13. Srivastava A, Singh RM. Vilsmeir-Haack reagent: A facile synthesis of 2-chloro-3-formylquinoline from N-arylacetamide and transformation into different functionalities. Indian J. Chem. 2005; 44B: 1886-1875.
14. Bouraiou A, Menasra H, Debache A, Rhouati S, Belfaitah A. Synthesis of some functionalized quinolyl aziridine derivatives. J. Soc. Alger. Chim. 2006; 16: 171-183.
15. Khan FN, Subashini R, Kushwaha A K, Hathwar VR, Ng SW. 2-Chloro-8-methyl quinoline-3-carbaldehyde. Acta Cryst. 2009; E65E: o2722.
16. Meth-Cohn O, Narine B, Tarnowski B. A versatile new synthesis of quinoline and related fused pyridines. Part-5. The synthesis of 2-chloroquinoline-3-carboxaldehyde. J Chem Soc. Perkin Trans. 1981; I: 1520-1530.
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01-07-2014
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“CONTRIBUTION OF NMR SPECTROSCOPY, MASS SPECTROMETRY AND X-RAY DIFFRACTOMETRY TECHNIQUES TO THE CHARACTERIZATION OF 2-CHLORO-8-METHYL-3-FORMYLQUINOLINE”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 3, July 2014, pp. 193-6, https://doi.org/10.25004/IJPSDR.2014.060304.
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How to Cite
“CONTRIBUTION OF NMR SPECTROSCOPY, MASS SPECTROMETRY AND X-RAY DIFFRACTOMETRY TECHNIQUES TO THE CHARACTERIZATION OF 2-CHLORO-8-METHYL-3-FORMYLQUINOLINE”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 3, July 2014, pp. 193-6, https://doi.org/10.25004/IJPSDR.2014.060304.
