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Synthesis of (3,4-bis{[2-hydroxy-3-methoxy-5-(4-methylphenyl azo)benzylidene]-amino}phenyl) phenyl methanone as a novel azo Schiff base
 
 
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Volume 2004
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10.3390/M377
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Short Note

Synthesis of novel azo Schiff base bis[5-(4-methoxyphenylazo)-2-hydroxy -3-methoxy benzaldehyde]-1,2-phenylene diimine

by
A. A. Jarrahpour
* and
M. Zarei
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
*
Author to whom correspondence should be addressed.
Molbank 2004, 2004(1), M377; https://doi.org/10.3390/M377
Submission received: 16 January 2004 / Accepted: 23 February 2004 / Published: 24 February 2004
Versions Notes

Schiff bases are a class of important compounds in medicinal and pharmaceutical field. They show biological activities including antibacterial [1,2,3,4], antifungal [5,6], anticancer [7,8,9], and herbicidal [10] activities . Furthermore, Schiff bases are utilized as starting material in the synthesis of industrial[11] and biological compounds such as β-lactams[12], etc. Azo compounds have been used for a long time as dyes in industry [13]. In addition, azo compounds are used in analytical chemistry as indicators in pH, redox, or complexometric titrations [14,15]. Some azo compouns have shown a good antibacterial activity [16,17]. The existence of an azo moiety in different types of compounds has caused them to show pesticidal activity [10]. Based on the mentioned properties for Schiff bases and azo compounds, we decided to synthesize a novel azo Schiff base 3. The biological and analytical uses of 3 are under study.
Molbank 2004 m377 i001
Azo aldehyde 2 was synthesized according to a reported method[18]. A mixture of 1,2-phenylene diamine 1 (0.50 g, 4.62 mmol) and 2-hydroxy-3-methoxy-5 (4-methoxyphenylazo) benzaldehyde 2 (2.65 g, 9.26 mmol) in absolute ethanol (40.00 mL) was refluxed for 3 hours to give a dark red precipitate. Then it was filtered and washed with ethanol to give pure azo Schiff base 3 (2.92 g, 98 %).
m.p. 85-187 oC.
IR (KBr) (cm-1): 1604.70 (HC=N), 3163.00-3672.20 (OH) .
,1H-NMR (CDCl3) (250 MHz) δ(ppm): 3.86 (2 OMe, s, 6H), 3.94 (2 OMe, s, 6H), 6.97-7.01(C6H4N2, m, 4H), 7.26-7.62 (2N2C6H4OMe, m, 8H), 7.85-7.89 (2HOC6H2OMe, m, 4H), 8.66 (2HC=N, s, 2H), 13.94 (2 OH, br, 2H) .
,13C- NMR (CDCl3) (62.90 MHz) δ(ppm): 55.93, 56.31, 105.45, 114.59, 120.07, 123.75, 124.76, 125.01, 128.39, 141.10, 145.10, 147.20, 150.12, 156.85, 163.26
MS (m/z, %): 388 (HOMeOC6H2C=NC6H4N=CC6H2OHOMeN, 2.6), 374 (C6H4(N=CC6H2 OHOMe)2, 55.3), 360 (C6H4N=CC6H2OHOMeN=NC6H4OMe, 2.3), 239 (C6H4N=CC6H2OHOMeN, 21.4), 225 (C6H4N=CC6H2OHOMe, 2.6), 135 (MeOC6H4N=N, 28.8), 107 (MeOC6H4, 100.0) .

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No. 81-SC-1540-C220).

References

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  18. Furniss, B. S.; Hannaferd, A. J.; Rogers, V.; Smith, P. W. G.; Tatchell, A. R. Vogel’s Textbook of Practical Organic Chemistry, 4th ed.; Longman Inc.: New York, 1981; p. 716. [Google Scholar]
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MDPI and ACS Style

Jarrahpour, A.A.; Zarei, M. Synthesis of novel azo Schiff base bis[5-(4-methoxyphenylazo)-2-hydroxy -3-methoxy benzaldehyde]-1,2-phenylene diimine. Molbank 2004, 2004, M377. https://doi.org/10.3390/M377

AMA Style

Jarrahpour AA, Zarei M. Synthesis of novel azo Schiff base bis[5-(4-methoxyphenylazo)-2-hydroxy -3-methoxy benzaldehyde]-1,2-phenylene diimine. Molbank. 2004; 2004(1):M377. https://doi.org/10.3390/M377

Chicago/Turabian Style

Jarrahpour, A. A., and M. Zarei. 2004. "Synthesis of novel azo Schiff base bis[5-(4-methoxyphenylazo)-2-hydroxy -3-methoxy benzaldehyde]-1,2-phenylene diimine" Molbank 2004, no. 1: M377. https://doi.org/10.3390/M377

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