M531 - Synthesis of 2-[4-(2-chlorobenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl]acetohydrazide

Molbank 2007, M531

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

Synthesis of 2-[4-(2-chlorobenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl]acetohydrazide

Nour-Eddine Benchat *, Abderrahmane Anaflous, Said Abouricha, Brahim El-Bali and Mohamed Ramdani

Department of Chemistry, University Mohamed I, Sciences Faculty, 60000 Oujda, Morocco

*Author to whom correspondence should be addressed. E-mail: [email protected]

Received: 3 January 2006 / Accepted: 24 June 2006 / Published: 31 May 2007

Keywords: pyridazin-3(2H)-one, N-alkylation, anticonvulsive agents.

Pyridazines are of chemical and biological interest. They have been reported to be anticonvulsive agents [1], [2]. Furthermore, BELLASIO et al. have described the antihypertensive effects of hydrazinopyridazine compounds [3]. In continuation of this line of investigation, we have synthesized compound (I); it will be subjected to further pharmacological investigations, especially tests of its anticancer activity.

To ( 0.96 g, 3 mmol) of ethyl [4-(2-chlorobenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl)] acetate (I), was added 10 ml of hydrazine hydrate. The mixture was placed in a pyrex tube which was then introduced into a Maxidigest MX 350 Prolabo microwave[4] monomode reactor and refluxed for 10 min on 60 w as irradiation power. After cooling, the product precipitates, and then is recristallised in absolute ethanol, yield : 80 % of (II) solid.

Melting point: 201-205°C

IR (KBr, cm^-1): 3352(NH), 1682 , 1469 , 1622 (C = O)

¹HNMR (300.14 MHz, CDCl₃) d (ppm): 2.49 (s, 3H, CH₃), 3.97 (s, 2H, CH₂), 4.21 (s, 2H, NH₂), 4.52 (s, 2H, CH₂), 6.03 (s, 1H, H4), 7.53 (m, 4H, H aromatic), 9.24 (s, 2H, NH₂).

¹³CNMR (75 MHz, CDCl₃) d (ppm): 19.38 (CH₃), 35.6 (CH₂), 52.76 (CH₂), 126.98 (CH aromatic), 128.85 (CH aromatic), 130.25 (CH aromatic), 130.68 (CH aromatic), 132.6 (CH aromatic), 134.54, 135.43, 144.93, 146.03, 160.31 (C=O), 167.16 (C=O).

References:

1. Wermuth, C.G.; Leclerc, G.; Melounov, P. Chim. Ther. 1971, 2, 109.

2. Laborit, H.; Weber, B.; Wermuth, C.G.; Delbarre, B.; Chekler, C.; Baron, C.; Rosen Garten, H. AGRESSOLOGIE 1965, 6, 415.

3. Bellasio, E. ; Parravicini, F. ; Testa, E. Il Farmaco Ed Sci. 1969, 11, 919.

4. (a) Kappe, C.O.; Dallinger, D. Nature Reviews Drug Discovery 2006, 5, 51; (b) De la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.