4-{[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]amino}benzoic acid

Mohamed El Kodadi; Fouad Malek; Abdelkrim Ramdani

doi:10.3390/M368

,

and

Laboratory of Chemistry Organic-Physics, Department of Chemistry, Faculty of Sciences, University Mohammed The First, BP 524-60 000 Oujda, Morocco.

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Author to whom correspondence should be addressed.

Molbank2004, 2004(1), M368;https://doi.org/10.3390/M368

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Keywords:

pyrazole; ligand; aminoacid

A mixture of (3,5-dimethyl-1H-pyrazol-1-yl)methanol 1 [] (1.84 g, 14.6 mmol) and 4-aminobenzoic acid 2 (1g, 7.3 mmol) in acetonitrile (50 mL) was stirred in a closed vessel at room temperature for 6 days [,,]. The white precipitate was filtred off, washed with acetonitrile and dried in air.

Yield: (1.54g, 68.5%).

Melting Point = 210-212°C (CH₃CN).

IR (KBr, cm^-1): 3260(s, NH), 3140, 3100, 3040, 3000, 2840, 2700, 2620, 1700(s, C=O), 1600 (s, C=C), 1550(s, C=N), 1420(s, C-N), 1260(s, -C-OH), 1150(s).

¹H NMR (400 MHz, DMSO-d₆) d ppm: 7.63 (d, 2H, Ph, J= 5.71 Hz); 7.35 (t, 1H, -NH, J= 3.42Hz); 6.8 (d, 2H, Ph, J= 5.71 Hz); 5.7 (s,1H, Pz); 5.25 (d, 2H, N-CH₂- N, J=3.42 Hz); 2.22(s, 3H, CH₃); 1.95(s, 3H, CH₃).

¹³C NMR (100 MHz, DMSO-d₆) d ppm: 167.51(C1), 150.91(C5), 145.65(C3), 138.71(C2), 131.02(C4), 118.95(C7), 112.04(C10), 105.47(C9), 56.39(C6), 13.42(C8), 10.75(C11).

FAB MS: 246[M+1].

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

Sorrel, T. N.; Vankai, V. A.; Garrity, M. L. Inorg. Chem. 1991, 30, 207.
Malachowski, M. R.; Davidson, M. G.; Hoffman, J. N. Inorg. Chim. Acta 1989, 157, 91.
Sheu, S. C.; Tien, M. J.; Cheng, M. C.; Ho, T. I.; Peng, S. M.; Lin, Y. C. J. Chem. Soc. Dalton Trans. 1995, 3503.
Touzani, R.; Ramdani, A.; Ben-Hadda, T.; El Kadiri, S.; Maury, O.; Le Bozec, H.; Dixneuf, P. H. Synth. Commun. 2001, 31, 1315.

Sample Availability: Available from the Authors.

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