3-Ethoxycarbonyl-1,4-dihydro-2-methylquinoline
Camara Hadietou Diadié, Attar Khalid, Boutayeb Mohammed, Benchidmi Mohamed and Essassi El Mokhtar
Laboratory of Organic Chemistry, Departement of Chemistry, Faculty of Sciences, University Mohammed V,BP 1014-Rabat, Morocco. E-mail : [email protected], [email protected], [email protected]
Received: 28 May 2001 / Accepted: 14
December 2001 / Published: 20 December 2001
Compound 1 [1] (1.23 g, 4.94 mmol ) and 0.1 g of Pd/C (10%) in 50 ml of ethanol are introduced into an hydrogenation reactor. The mixture is first degassed under reduced pressure and then left at normal pressure. When the reaction is finished (at end of hydrogen consumption), the solution is filtered under vacuum and then concentrated under reduced pressure. The residue is purified by column chromatography on silica gel. (hexane / ethyl acetate 60/40). Compound 2 was obtained in 60% yield.
M.P.130-132 °C.
TLC ( Hexane/EtOAc 6:4 ): Rf 0.60.
IR ( KBr, cm –1) : 3395, 1725, 1608.
1H-NMR ( CDCl3 ) : 6.43 – 7.04 (m ,4H); 4 (q, 2H. J= 7.2Hz ); 4.02 (broad, NH); 3.04 (q, 2H, JAB= 17.1Hz); 1.56 (s, 3H); 1.1 (t, 3H, J= 7.2Hz).
NMR : 4.02 (broad, NH).
MS (EI): m/z : 217; 216; 188; 144; 106 (100); 77.
References
1. Gordon, E. H.; Hughes, D.; Rae, D.; Rhodes, A. P. Tetrahedron Letters 1967, 3, 241-246.
Sample Availability: Available from the authors and from MDPI.
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