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4-(3-Nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one

1
Department of Chemistry, Faculty of Science, United Arab Emirates University, P.O.Box 17551 Al-Ain, UAE
2
Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M261; https://doi.org/10.3390/M261
Submission received: 5 June 2001 / Accepted: 15 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 06 m261 i001
To a cold solution of 5-trifluoromethyl-2,4-dihydropyrazol-3-one [1,2] (0.76 g, 5 mmol) in ethanol (25 ml) containing sodium acetate (0.82 g, 10 mol), 3-nitrobenzenediazonium chloride ( 5 mmol) was added dropwise with stirring at 0-5°C. The reaction mixture was stirred at room temperature for three hours and the precipitated crude product was filtered, washed with water, dried and crystallized from ethanol to give 1.2 g (80%) of 2 as orange crystals.
M.p. 253-255oC. MS (m/z): 301.
1H-NMR (250 MHz, DMSO-d6): 2.50(s, 1H, CH); 7.71-8.45(m, 4H, aromatic CH); 12.70(s, 1H, NH).
13C-NMR (75 MHz, CDCl3): 116.65, 124.24(quaternary aromatic carbons); 111.04, 119.99, 122.40, 130.77(4 aromatic CH’s); 136.50(q, CF3); 142.38(C-4); 148.35(C-5); 158.33(CO).

Supplementary Materials

References

  1. Poulter, C.D.; Wiggins, P.L.; Plummer, T.L. J. J. Org. Chem. 1981, 46, 1532. [CrossRef]
  2. Zohdi, H.F.; Elghandour, A.H.H.; Rateb, N.M.; Sallam, M.M.M. J. J. Chem. Res. 1992, (S) 396, (M) 3015.
Sample Availability: Available from the authors.

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MDPI and ACS Style

Zohdi, H.F.; Rateb, N.M.; Haikal, A.Z. 4-(3-Nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one. Molecules 2001, 6, M261. https://doi.org/10.3390/M261

AMA Style

Zohdi HF, Rateb NM, Haikal AZ. 4-(3-Nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one. Molecules. 2001; 6(12):M261. https://doi.org/10.3390/M261

Chicago/Turabian Style

Zohdi, Hussein F., Nora M. Rateb, and A. Z. Haikal. 2001. "4-(3-Nitrophenylazo)-5-trifluoromethyl-2,4-dihydropyrazol-3-one" Molecules 6, no. 12: M261. https://doi.org/10.3390/M261

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