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Short Note

Synthesis of Ethyl (4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetate

by
Nour-Eddine Benchat
*,
Abderrahmane Anaflous
,
Said Abouricha
,
Mohammed Ramdani
and
Abderazak Benalla
Department of Chemistry, University Mohamed I, Sciences Faculty, 60000 Oujda, Morocco
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(2), M529; https://doi.org/10.3390/M529
Submission received: 3 January 2006 / Accepted: 24 June 2006 / Published: 31 May 2007
Wermuth and coll [1] synthesized a series of products by alkylation of pyridazines, Laborit [2] showed that these products are good analgesics and have a low toxicity. 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.
Molbank 2007 m529 i001
The product (II) was prepared from 5-benzyl-6-methylpyridazin-3(2H)-one (I) in situ by the solid-liquid PTC conditions without solvent[3]. To pyridazin (I) (1.2 g, 6 mmol) was added (2.75 g, 9 mmol) of potassium carbonate, (0.3 g, 1 mmol) of TBAB and (1 g, 6 mmol) of 2-ethyl bromoacetate. The mixture was placed in a pyrex tube which was then introduced into a Maxidigest MX 350 Prolabo microwave monomode reactor fitted with a rotational system. At the end of the irradiation time (10 min on 90 w as irradiation power), the mixture was cooled to ambiant temperature. After elution with ethyl acetate (30 ml) and subsequent filtration on florisil, the organic product was purified by chromatography on silicagel using CH2Cl2 as eluent, yield : 96 % of (II) solid.
Melting point: 89-93°C
IR (KBr, cm−1): 1740 (CO2Et), 1603, 1469, 1211 (C = N).
1H-NMR (300.14 MHz, CDCl3) d (ppm): 1.29 (t, J=5Hz, 3H, CH3), 2.23 (s, 3H, CH3), 3.78 (s, 2H, CH2), 4.26 (q, J = 5Hz, 2H, CH2), 6.53 (s, 1H, H4), 7.12 (d, J = 7.5Hz, 2H, aromatic protons), 7.25 (m, 3H, aromatic protons).
13C-NMR (75 MHz, CDCl3) d (ppm):19.12(CH3), 38.45 (CH2), 52.67 (CH2), 61.65 (CH2), 127.26 (CH aromatic), 127.97 (CH aromatic), 129.02 (2 CH aromatic), 129.11 (2 CH aromatic), 135.61, 145.21, 146.42, 160.38 (C3), 167.74 (C=O).
MS: m/z (%): M+= 287, 241.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

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. [PubMed]
  3. (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. [PubMed]

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MDPI and ACS Style

Benchat, N.-E.; Anaflous, A.; Abouricha, S.; Ramdani, M.; Benalla, A. Synthesis of Ethyl (4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetate. Molbank 2007, 2007, M529. https://doi.org/10.3390/M529

AMA Style

Benchat N-E, Anaflous A, Abouricha S, Ramdani M, Benalla A. Synthesis of Ethyl (4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetate. Molbank. 2007; 2007(2):M529. https://doi.org/10.3390/M529

Chicago/Turabian Style

Benchat, Nour-Eddine, Abderrahmane Anaflous, Said Abouricha, Mohammed Ramdani, and Abderazak Benalla. 2007. "Synthesis of Ethyl (4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetate" Molbank 2007, no. 2: M529. https://doi.org/10.3390/M529

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