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Volume 2004
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10.3390/M371
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Short Note

Synthesis of 2-hydroxy-3-methoxy-5-(4-methoxyphenylazo) benzaldehyde. A new aldehyde for the preparation of biologically active molecules.

by
A. A. Jarrahpour
*,
A. R. Esmaeilbeig
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), M371; https://doi.org/10.3390/M371
Submission received: 8 October 2003 / Accepted: 20 February 2004 / Published: 24 February 2004
Versions Notes

Diazo compounds have interesting biological activities [1,2,3,4]. It was shown that the presence of an azo functionality in many compounds is essential for the exhibition of pesticidal activity [5]. In addition, the existence of the methoxy groups on some molecules enhanced the biological activities [6]. As such, we synthesized a new aldehyde 4 possessing an azo as well as the methoxy groups. Reaction of this novel azoaldehyde with various aromatic amines afforded the corresponding Schiff bases. Their antibacterial and antifungal activities are under study to be presented in the near future.
Molbank 2004 m371 i001
Experimental: A solution of aqueous HCl (1.61 mL, 17.92 mmol ) in 20 mL water was added to the p-anisidine 1 (1.00 g, 8.12 mmol). It was stirred and cooled to 0 oC and then an aqueous solution of NaNO2 (0.62 g ,9.00 mmol ,8 mL H2O) was added dropwise. The so-formed diazonium chloride 2 was consecutively coupled with o-vanillin 3 (1.24 g , 8.12 mmol ), dissolved in 10.00 mL of aqueous 2N NaOH (0.80 g, 20.00 mmol ). The reaction mixture was stirred for 1 hour at 0 oC, and then allowed to warm-up slowly to room temperature. The brown precipitate thus obtained was filtered and washed with H2O (3 x 20 mL ). Then it was dissolved in CH2Cl2 and dried (Na2SO4), filtered, and the solvent was evaporated under reduced pressure [7]. The crude product was purified by column chromatography (silica gel, CH2Cl2/n-hexane, 1:1, V/V as eluant) to give 2-hydroxy-3-methoxy-5-(4-methoxyphenylazo)benzaldehyde 4 (1.77 g, 6.18 mmol) in 76.20 % yield.
m.p. 169-171 oC.
IR (KBr) (cm-1): 1600 (C=C) , 1670 (C=O) , 3030-3580 ( OH ) .
1H-NMR (CDCl3) (250 MHz) δ (ppm): 4.01(6H, s, 2OCH3), 7.07-8.26 (6H, m, aromatic hydrogens), 10.06 (1H , s, CHO), 12.78 (1H, br, OH).
13C-NMR (CDCl3) (62.90 MHz) δ (ppm): 56.82 (OCH3), 108.70-125.19 (aromatic carbons), 196.91 (CHO).
MS (m/z, %): 286 (M+, 65.5), 151 ( Molbank 2004 m371 i002, 19.8), 135 (MeOC6 H4N2, 40.3),107 (MeOC6 H4, 100), 92 (C6H4O, 20.3).

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-1495-C191).

References

  1. Pathak, P.; Jolly, V.S.; Sharma, K.P. Orient. J. Chem. 2000, 16(1), 161–162.
  2. Pathak, P.; Jolly, V.S.; Sharma, K.P. Orient. J.Chem. 2000, 16(3), 493–494.
  3. Alka, Pradhan; Vinod, Pradhan; Jolly, V.S. Orient. J. Chem. 1994, 10, 73–74.
  4. Jolly, V. S.; Pathak, M.; Jain, R. J .Indian. Chem .Soc 1993, 70, 505–507.
  5. Samadhiya, S.; Halve, A. Orient. J. Chem. 2001, 17(1), 119–122.
  6. Halve, A.; Goyal, A. Orient. J. Chem. 1996, 12(1), 87–88.
  7. 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]
  • Samples Availability: Available from MDPI.

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MDPI and ACS Style

Jarrahpour, A.A.; Esmaeilbeig, A.R.; Zarei, M. Synthesis of 2-hydroxy-3-methoxy-5-(4-methoxyphenylazo) benzaldehyde. A new aldehyde for the preparation of biologically active molecules. Molbank 2004, 2004, M371. https://doi.org/10.3390/M371

AMA Style

Jarrahpour AA, Esmaeilbeig AR, Zarei M. Synthesis of 2-hydroxy-3-methoxy-5-(4-methoxyphenylazo) benzaldehyde. A new aldehyde for the preparation of biologically active molecules. Molbank. 2004; 2004(1):M371. https://doi.org/10.3390/M371

Chicago/Turabian Style

Jarrahpour, A. A., A. R. Esmaeilbeig, and M. Zarei. 2004. "Synthesis of 2-hydroxy-3-methoxy-5-(4-methoxyphenylazo) benzaldehyde. A new aldehyde for the preparation of biologically active molecules." Molbank 2004, no. 1: M371. https://doi.org/10.3390/M371

APA Style

Jarrahpour, A. A., Esmaeilbeig, A. R., & Zarei, M. (2004). Synthesis of 2-hydroxy-3-methoxy-5-(4-methoxyphenylazo) benzaldehyde. A new aldehyde for the preparation of biologically active molecules. Molbank, 2004(1), M371. https://doi.org/10.3390/M371

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