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Short Note

4-[(Anthracen-9-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one

by
Abdullah M. Asiri
1,2,* and
Salman A. Khan
1
1
Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah, Saudi Arabia
2
The Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, P.O. Box 80203, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molbank 2011, 2011(2), M725; https://doi.org/10.3390/M725
Submission received: 24 March 2011 / Accepted: 6 May 2011 / Published: 9 May 2011
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Abstract

:
The title compound, 4-[(anthracen-9-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one (3), was synthesized in high yield by reaction of anthracene-9-carbaldehyde and 4-aminoantipyrine in ethanol. The structure of this new compound was confirmed by elemental analysis, IR, 1H NMR, 13C NMR and GC-MS spectral data.

Graphical Abstract

Nitrogen-atom containing heterocyclic compounds are an important subset of the natural products that exhibit biological activities, including antitumor [1], antiamoebic [2], antimicrobial [3] and anti-inflammatory [4] activities. Pyrazol-3-one presents an interesting group of compounds, many of which possess widespread pharmacological properties such as analgesic, antipyretic, and antirheumatic activities [5]. These derivatives are also well known for their pronounced anti-inflammatory properties [6] and are used as potent antidiabetic agents [7] Pyrazol-3-one containing Schiff bases can show even increased biological activity [8]. Since the pyrazol-3-one Schiff base moiety seems to be a possible pharmacophore in various pharmacologically active agents, we decided to synthesize a new pyrazol-3-one containing a Schiff base unit by reaction of anthracene-9-carbaldehyde with 4-aminoantipyrine.

Experimental

A mixture of anthracene-9-carbaldehyde (0.50 g, 0.0024 mol) and 4-aminoantipyrine (0.49 g, 0.0024 mol) in ethanol (15 mL) was heated for 3 h at 80 °C. The reaction was monitored by TLC (chloroform/methanol, 9:1). The solid that separated from the cooled mixture was collected and recrystallized from a methanol/chloroform mixture (8:2) to give the title compound (3) as a yellow solid.
Yield: 87%; m.p. 231–232 °C
GC-MS m/z (rel. int.%): 393 (68) [M+1]+
IR (KBr) vmax cm-1: 3027 (Ar-H, stretch), 2874 (C-H), 1636 (C=O), 1580 (HC=N), 1138 (C-N)
1H NMR (600 MHz, CDCl3) (δ/ppm): 11.06 (s, CHolefinic), 8.98 (d, J = 8.84 Hz, CH), 8.50 (d, J = 7.4 Hz, CH), 8.04 (dd, J = 7.6 Hz, CH), 7.50 (dd, J = 7.2 Hz, CH), 7.48 (s, CH), 7.56–7.51 (m, 5H, CH), 3.23 (s, CH3), 2.19 (s, CH3)
13C NMR (150 MHz, CDCl3) δ: 160.84, 157.70, 152.03, 134.75, 131.54, 130.45, 129.32, 129.01, 128.8, 127.11, 126.60, 125.64, 125.22, 124.62, 119.70, 35.78, 10.36
Anal. calc. for C26H21N3O: C, 79.77, H, 5.41, N, 10.73. Found: C, 79.74, H, 5.38, N, 10.68.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing the research facilities.

References

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Molbank 2011 m725 g001 550
Figure 1. Synthesis of compound 3.
Figure 1. Synthesis of compound 3.
Molbank 2011 m725 g001

Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A. 4-[(Anthracen-9-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one. Molbank 2011, 2011, M725. https://doi.org/10.3390/M725

AMA Style

Asiri AM, Khan SA. 4-[(Anthracen-9-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one. Molbank. 2011; 2011(2):M725. https://doi.org/10.3390/M725

Chicago/Turabian Style

Asiri, Abdullah M., and Salman A. Khan. 2011. "4-[(Anthracen-9-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one" Molbank 2011, no. 2: M725. https://doi.org/10.3390/M725

APA Style

Asiri, A. M., & Khan, S. A. (2011). 4-[(Anthracen-9-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one. Molbank, 2011(2), M725. https://doi.org/10.3390/M725

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