Green synthesis is the design of chemical products and processes that reduces or eliminates the use and generation of hazardous substances. Schiff bases of 4-hydroxy-3- methoxybenzaldehyde (vanillin) were prepared using various aromatic amines and base catalyst in the presence of aqueous media. High performance liquid chromatography (HPLC) and ultraviolet (UV) spectrophotometry methods were developed for qualitative study of the synthesized 4-hydroxy-3- methoxybenzaldehyde Schiff bases. HPLC was carried out by reversed phase on a C18 column with a mobile phase composed of acetonitrile and 0.5% triethyl amine (pH 4.5 adjusted with orthophosphoric acid (60:40, v/v)). UV measurements were performed at λmax 286 nm for compound V1 ((E)-4-(4-hydroxy-3-methoxybenzylideneamino)benzoic acid), λmax 336 nm for compound V2 ((E)-4-(4-hydroxy-3-methoxybenzylideneamino)phenol), and λmax 320 nm for compound V3 ((2-methoxy-4-(E)-(phenylimino)methyl)phenol). Both the HPLC and UV methods showed good reproducibility and precision and were successfully applied to study 4-hydroxy-3- methoxybenzaldehyde derivatives. The standard de-viations of relative peak area and retention times for 4-hydroxy-3-methoxybenzaldehyde derivatives were within 2% indicating the suitability of the system. The proposed economical methods can be applied for rou-tine analysis of 4-hydroxy-3-methoxybenzaldehyde derivatives of any type.
Similar content being viewed by others
References
P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York (1998), p. 30
J. H. Clarck, Nat. Chem., 1, 12 – 13 (2009).
W. Al Zoubi, Int. J. Org. Chem., 3, 73 – 95, (2013).
D. Lednicer and L. A. Mitscher, The Organic Chemistry of Drug Synthesis, Wiley Interscience, New York (1984), Vol. III, pp. 283 – 285.
K. Nagarjun and A. Majumdar, Medicinal Chemistry Theory and Practicals, Birla Publication Pvt. Ltd, India (2008), pp. 12 – 18.
S. Tabassum, S. Amir, F. Arjmand, et al., Eur. J. Med. Chem., 60, 216 – 232 (2013).
M. Neelakantan, M. Esakkiammal, S. Mariappan, et al., Ind. J. Pharm. Sci., 72, 216 – 222 (2010).
M. B. Fugu, N. P. Ndahi, B. B. Paul, and A. N. Mustapha, J. Chem. Pharm. Res., 5, 22 – 28 (2013).
V. Cardile, A. M. Panico, A. Geronikaki, et al., Farmaco, 57, 1009 – 1113 (2002).
C. H. Sridevi, J. Med. Bioeng., 4, 363 – 366 (2014).
S. J.Wadher, M. P. Puranik, N. A. Karande, and P. G. Yeole, Int. J. Pharm. Tech. Res., 1, 22 – 33 (2009).
D. A. Skoog, Analytical Chemistry, 7th ed., Saunders College Publishers, Philadelphia (1996), pp. 1 – 15.
W.W. Brain and D. Cooper, Samples and Standards: Analytical Chemistry by Open Learning, John Wiley & Sons, London (1991), pp. 2 – 5.
R. D. Braun, Introduction to Instrumental Analysis, McGraw-Hill Book Company, New York (1987), pp. 1 – 13.
G. H. Jeffery and J. Basselt, Vogel’s Text Book of Quantitative Chemical Analysis, 5th ed., (1991), pp. 217 – 235.
A. M. Knevel, F. E. Digangi, Jenkin’s Quantitative Pharmaceutical Chemistry, McGraw-Hill Book Company, New York (1989), pp. 21 – 23.
S. Lindsay, HPLC by open Learning, John Wiley & Sons, New York, (1991), pp. 30 – 45.
L. R. Snyde, J. J. Kirkland, and J. L. Glajch, Practical HPLC Method Development, 2nd ed., John Wiley & Sons, New York (1997), pp. 1 – 14.
J. W. Robinson, Undergraduate Instrumental Analysis, 5th ed., Marcel Dekker, New York (1997), pp. 584 – 589.
M. Zarei and A. Jarrahpour, Iran. J. Sci. Technol., A3, 235 – 242 (2011).
A. R. Bendale, K. Darsheen, D. P. Damahe, S. P. Narkhede, A. G. Jadhav, and G. Vidyasagar, Der Chem. Sin., 3, 34 – 38 (2011).
G. Kaupp, Cryst. Eng. Comm., 11, 388 – 403 (2009).
Validation of Analytical Procedures: Methodology, ICH Harmonized Tripartite Guidelines (1996), pp. 1 – 8.
Acknowledgments
The authors are thankful to AIMST University for financial support in the form of AIMST grant (AURGC/14/FOP/2013).
Conflict of Interest
The authors declare no conflict of interest.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Chigurupati, S., Muralidharan, S., Cin, L.S. et al. Studying Newly Synthesized and Developed 4-Hydroxy-3-Methoxybenzaldehyde Schiff Bases by UV Spectrophotometry and High Performance Liquid Chromatography. Pharm Chem J 50, 851–856 (2017). https://doi.org/10.1007/s11094-017-1544-0
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-017-1544-0