Molbank 2006, M485

http://www.mdpi.org/molbank/

 

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

 

R. Bouhfid, E.M. Essassi*

 

Laboratoire de Chimie Organique H¨¦t¨¦rocyclique, Universit¨¦ Mohammed V-Agdal, BP: 1014 Avenue Ibn Batouta, Rabat, Maroc.

E-mail : [email protected]

*Author to whom correspondence should be addressed

 

Received: 10 February 2006 / Accepted: 20 March 2006 / Published: 1 September 2006

 

Keywords: quinoline, hydrazide, condensation.

 

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.

 

           

 

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 ¡ãC.

 

¹H-NMR (300 MHz, DMSO): ¦Ä= 4.67 (NH2); 6.54 (s, 1H, =CH); 7.35-7.78 (m, 3H, HAr); 9.93 (NH).

 

¹³C-NMR (300 MHz, DMSO): ¦Ä= 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 %;

 

Reference

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, 5, 517.

3- El Otmani B., El Hakmaoui A., Fifani J.,Essassi E.M.,Gueiffier A., C. R. Acad. Sci. Paris t-2, s¨¦rie IIc, 2001, 4, 285.

 

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