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Volume 2006
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10.3390/M485
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Short Note

Synthesis of 6-chloro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide

by
R. Bouhfid
and
E.M. Essassi
*
Laboratoire de Chimie Organique Hétérocyclique, Université Mohammed V-Agdal, BP: 1014 Avenue Ibn Batouta, Rabat, Maroc
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(5), M485; https://doi.org/10.3390/M485
Submission received: 10 January 2006 / Accepted: 20 March 2006 / Published: 1 September 2006
Versions Notes

In previous works we have shown that hydrazides are highly useful starting materials and intermediates in the synthesis of several heterocyclic compounds1-3 of potential biological activities.
The aim of this work is to describe the preparation of a novel compound entitled 6-chloro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide.
Molbank 2006 m485 i001
To a solution of ethyl 2-oxo-1,2-dihydroquinoline-4-carboxylate 1 (1g, 3.9 mmol) in ethanol, was added hydrazine hydrate 80 % (0.22 mL, 4.6 mmol). The mixture was refluxed for 24h and ice-water was added. The precipate was filtered and recrystallised from ethanol to afford 0.73 g (70 % yields) of product 2.
Melting point: > 250 °C.
1H-NMR (300 MHz, DMSO): δ= 4.67 (NH2); 6.54 (s, 1H, =CH); 7.35-7.78 (m, 3H, HAr); 9.93 (NH).
13C-NMR (300 MHz, DMSO): δ= 121.8 (=CH); 118.0, 125.4, 131.2 (CHAr); 114.8, 126.3, 139.3, 139.9 (Cq); 161.3 (C=O); 165.0 (CON2H3).
MS (EI, m/z): 237.
Elemental analysis: Calculated for C10H8ClN3O2: C, 50.54 %; H, 3.39 %; N, 17.68 %; Found: C, 50.60 %; H, 3.42 %; N, 17.74 %;

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Essassi, EM.; Fifani, J. Bull. Soc. Chem. Belg. 1987, 96, 63.
  2. El Otmani, B.; El Mahi, M.; Essassi, E.M. C. R. Chimie 2002, 2, 517.
  3. El Otmani, B.; El Hakmaoui, A.; Fifani, J.; Essassi, E.M.; Gueiffier, A. C. R. Acad. Sci. Paris t-2, série IIc 2001, 4, 285.

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MDPI and ACS Style

Bouhfid, R.; Essassi, E.M. Synthesis of 6-chloro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide. Molbank 2006, 2006, M485. https://doi.org/10.3390/M485

AMA Style

Bouhfid R, Essassi EM. Synthesis of 6-chloro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide. Molbank. 2006; 2006(5):M485. https://doi.org/10.3390/M485

Chicago/Turabian Style

Bouhfid, R., and E.M. Essassi. 2006. "Synthesis of 6-chloro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide" Molbank 2006, no. 5: M485. https://doi.org/10.3390/M485

APA Style

Bouhfid, R., & Essassi, E. M. (2006). Synthesis of 6-chloro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide. Molbank, 2006(5), M485. https://doi.org/10.3390/M485

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