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Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivative

Received: 7 January 2021     Accepted: 6 February 2021     Published: 17 March 2021
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Abstract

Background: Looking at the previous studies on quinazolinones derivatives, only limited information’sare available on their massspectral along with the preparation of novel quinazolin-4-(3H)-one derivatives. Consolidation of Methyl-2-amino-4-Chlorobenzoate with acetic anhydride produced the cyclic compound 2-methyl 7-Chloro-1, 3-benzo-oxazine-4-one (1) which then produced 3-Amino-2-Methyl 7-Chloro quinazolin-4(3H)-ones (2) through the reaction with hydrazine hydrate. These compounds synthesized were indisputably confirmed by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography-Mass spectrophotometry and Elemental analysis. Discussion: The molecular ion of m/z 235 fragments to give m/z 220 by loss of –NH group. The ion of m/z 220 was broken to give m/z 206 by losing CH2 group and fragment to m/z 177 by loss of HCO. This fragmented to m/z 162 by loss of –CH3 group and then m/z 136 by loss of CN group. The loss of O gave m/z 120 which fragment to give m/z 93 by loss of –HCN and finally gave m/z 65 by loss of CO group. Conclusion: The electron impact ionization mass spectra of compound 2 show a weak molecular ion peak and a base peak of m/z 235 resulting from a cleavage fragmentation. Compound 2 give a characteristic fragmentation pattern. From the study of the mass spectra of compound 2, it was found that the molecular ion had fragmented to the m/z 220. The final fragmentation led to ion of m/z 93 and ion of mass m/z 65, respectively.

Published in American Journal of Materials Synthesis and Processing (Volume 6, Issue 1)
DOI 10.11648/j.ajmsp.20210601.13
Page(s) 20-25
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2021. Published by Science Publishing Group

Keywords

Mass Spectroscopy, 3-amino-7-chloro-2-methyl Quinazolinone, Nucleophile, Quinazolinone, Electron Impact Ionization Mass Spectra

References
[1] Kennedy, John F. An Introduction to Medicinal Chemistry. Carbohydrate Polymers 2007; 68: 609–610. http://dx.doi.org/10.1016/ j.carbpol.2006.06.032
[2] Selvam T, Kumar P, Vijayaraj P. Quinazoline Marketed drugs – A Review. Research in Pharmacy 2011; 1: 1-21.
[3] Stewart KD, Shirodaa M, James CA. Drug Guru: A computer software program for drug design using medicinal chemistry rules. Bioorganic & Medicinal Chemistry 2006; 14: 7011–7022. http://dx.doi.org/10.1016/ j.bmc.2006.06.024 PMid:16870456
[4] Maity A, Mondal S, Paira R, Hazra A, Naskar S, Sahu KB, Saha P, Banrejee S, Mondal NB. A novel approach for the one-pot synthesis of linear and angular fused quinazolinones Tetrahedron Lett 2011; 52: 3033-3037. http://dx.doi.org/10.1016/j.tetlet.2011.04.019
[5] Gundla R, Kazemi R, Sanam R, Muttineni R, Sarma JA, Dayam R, Neamati NJ. Discovery of Novel Small-Molecule Inhibitors of Human Epidermal Growth Factor Receptor-2: Combined Ligand and TargetBased Approach. Med. Chem 2008; 51: 3367. http://dx.doi.org/10.1021/jm7013875 PMid:18500794
[6] Balakumar C, Lamba P, Kishore DP, Narayan BL, Rao KV, Rajwinder K, Rao KR, Shireesha B, Narsaiah B. Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines. Eur. J. Med. Chem. 2010; 45: 4904–4913. http://dx.doi.org/10.1016/j.ejmech.2010.07.063 PMid:20800934
[7] Venakata Ramana Reddy et al, Int. J. Pharm. Sci. Rev. Res., 29 (2), 2014; Article No. 01, Pages: 1-4.
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[9] Nagaraju Gollapalli et al, AJPAMC, 1 (1), 2013, 48-53.
[10] Mohamed F. Zayed, Journal of Taibah University Medical Sciences (2014) 9 (2), 104–109.
[11] D. Channe Gowda et al, Bioorganic & Medicinal Chemistry Letters 25 (2015) 1072–1077.
[12] AMR Y Esmat et al, Lipids in Health and Disease 2005, 4: 22
[13] Nema Rajesh Kumar et al, Academic Journal of Cancer Research, 2009, 2 (2): 73-77.
[14] Mohammed Hussen Bule et al, IAJPR, 2015, Vol 5, Issue 02.
[15] B. Zarranz et al, Brazilian Journal of Pharmaceutical Sciences, 2006, vol. 42.
[16] CH. Rajveer et al, Int. J. Pharma and Bio Sci, 2010, Vol. 1, Issue-3, 2010.
[17] Ratnakar Singh et al, IJPCBS 2013, 3 (4), 1269-1275.
[18] Kishor H. Chikhalia et al, International Journal of Drug Design and Discovery, 2012, Volume 3, Issue 1, 739- 730.
[19] Sucheta et al, IJPCBS 2012, 2 (1), 97-103.
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    Osarumwense Peter Osarodion, Omotade Treasure Ejodamen. (2021). Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivative. American Journal of Materials Synthesis and Processing, 6(1), 20-25. https://doi.org/10.11648/j.ajmsp.20210601.13

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    ACS Style

    Osarumwense Peter Osarodion; Omotade Treasure Ejodamen. Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivative. Am. J. Mater. Synth. Process. 2021, 6(1), 20-25. doi: 10.11648/j.ajmsp.20210601.13

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    AMA Style

    Osarumwense Peter Osarodion, Omotade Treasure Ejodamen. Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivative. Am J Mater Synth Process. 2021;6(1):20-25. doi: 10.11648/j.ajmsp.20210601.13

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  • @article{10.11648/j.ajmsp.20210601.13,
      author = {Osarumwense Peter Osarodion and Omotade Treasure Ejodamen},
      title = {Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivative},
      journal = {American Journal of Materials Synthesis and Processing},
      volume = {6},
      number = {1},
      pages = {20-25},
      doi = {10.11648/j.ajmsp.20210601.13},
      url = {https://doi.org/10.11648/j.ajmsp.20210601.13},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajmsp.20210601.13},
      abstract = {Background: Looking at the previous studies on quinazolinones derivatives, only limited information’sare available on their massspectral along with the preparation of novel quinazolin-4-(3H)-one derivatives. Consolidation of Methyl-2-amino-4-Chlorobenzoate with acetic anhydride produced the cyclic compound 2-methyl 7-Chloro-1, 3-benzo-oxazine-4-one (1) which then produced 3-Amino-2-Methyl 7-Chloro quinazolin-4(3H)-ones (2) through the reaction with hydrazine hydrate. These compounds synthesized were indisputably confirmed by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography-Mass spectrophotometry and Elemental analysis. Discussion: The molecular ion of m/z 235 fragments to give m/z 220 by loss of –NH group. The ion of m/z 220 was broken to give m/z 206 by losing CH2 group and fragment to m/z 177 by loss of HCO. This fragmented to m/z 162 by loss of –CH3 group and then m/z 136 by loss of CN group. The loss of O gave m/z 120 which fragment to give m/z 93 by loss of –HCN and finally gave m/z 65 by loss of CO group. Conclusion: The electron impact ionization mass spectra of compound 2 show a weak molecular ion peak and a base peak of m/z 235 resulting from a cleavage fragmentation. Compound 2 give a characteristic fragmentation pattern. From the study of the mass spectra of compound 2, it was found that the molecular ion had fragmented to the m/z 220. The final fragmentation led to ion of m/z 93 and ion of mass m/z 65, respectively.},
     year = {2021}
    }
    

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  • TY  - JOUR
    T1  - Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivative
    AU  - Osarumwense Peter Osarodion
    AU  - Omotade Treasure Ejodamen
    Y1  - 2021/03/17
    PY  - 2021
    N1  - https://doi.org/10.11648/j.ajmsp.20210601.13
    DO  - 10.11648/j.ajmsp.20210601.13
    T2  - American Journal of Materials Synthesis and Processing
    JF  - American Journal of Materials Synthesis and Processing
    JO  - American Journal of Materials Synthesis and Processing
    SP  - 20
    EP  - 25
    PB  - Science Publishing Group
    SN  - 2575-1530
    UR  - https://doi.org/10.11648/j.ajmsp.20210601.13
    AB  - Background: Looking at the previous studies on quinazolinones derivatives, only limited information’sare available on their massspectral along with the preparation of novel quinazolin-4-(3H)-one derivatives. Consolidation of Methyl-2-amino-4-Chlorobenzoate with acetic anhydride produced the cyclic compound 2-methyl 7-Chloro-1, 3-benzo-oxazine-4-one (1) which then produced 3-Amino-2-Methyl 7-Chloro quinazolin-4(3H)-ones (2) through the reaction with hydrazine hydrate. These compounds synthesized were indisputably confirmed by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography-Mass spectrophotometry and Elemental analysis. Discussion: The molecular ion of m/z 235 fragments to give m/z 220 by loss of –NH group. The ion of m/z 220 was broken to give m/z 206 by losing CH2 group and fragment to m/z 177 by loss of HCO. This fragmented to m/z 162 by loss of –CH3 group and then m/z 136 by loss of CN group. The loss of O gave m/z 120 which fragment to give m/z 93 by loss of –HCN and finally gave m/z 65 by loss of CO group. Conclusion: The electron impact ionization mass spectra of compound 2 show a weak molecular ion peak and a base peak of m/z 235 resulting from a cleavage fragmentation. Compound 2 give a characteristic fragmentation pattern. From the study of the mass spectra of compound 2, it was found that the molecular ion had fragmented to the m/z 220. The final fragmentation led to ion of m/z 93 and ion of mass m/z 65, respectively.
    VL  - 6
    IS  - 1
    ER  - 

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Author Information
  • Department of Chemical Sciences, Ondo State University of Sciences and Technology, Okitipupa, Nigeria

  • Department of Chemical Sciences, Ondo State University of Sciences and Technology, Okitipupa, Nigeria

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