3-Ethoxycarbonyl-1,4-dihydro-2-methylquinoline

Camara Hadietou Diadié; Attar Khalid; Boutayeb Mohammed; Benchidmi Mohamed; Essassi El Mokhtar

doi:10.3390/M243

,

and

Laboratory of Organic Chemistry, Departement of Chemistry, Faculty of Sciences, University Mohammed V,BP 1014-Rabat, Morocco

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Author to whom correspondence should be addressed.

Molecules2001, 6(12), M243;https://doi.org/10.3390/M243

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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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 ): R_f 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, J_AB= 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

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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