THE SYNTHESIS OF 1,3-DIMETHYL-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE FROM METHYLEUGENOL : APPLICATION OF RITTER REACTION FOR DIRECTLY CYCLIZATION

https://doi.org/10.22146/ijc.21733

M. Farid Rahman(1*), Elvina Dhiaul Iftitah(2)

(1) Chemistry Department, Faculty of Mathematics and Sciences, Brawijaya University, Jl. Veteran, Malang
(2) Chemistry Department, Faculty of Mathematics and Sciences, Brawijaya University, Jl. Veteran, Malang
(*) Corresponding Author

Abstract


The synthesis of 1,3-dimethyl-6,7-dimethoxy-3,4-dihydroisoquinoline from methyleugenol with application of Ritter reaction for directly cyclization was presented. This research was carried out in 2 steps : (1) Determination of intermediate stability that undergo in the reaction by using hyperchem version 6 with AM 1 semi empirical method, and (2) Synthesis of dihydroisoquinoline from methyleugenol and acetonitrile with acid catalyst (H2SO4) in the laboratory. The result of AM 1 calculation found that generally, the intermediate encourage the formation dihydroisoquinoline product, had low energy were compared with the intermediate in other product. Therefore, the dihydroisoquinoline product was easily formed. The result of experimental laboratory found that dihydroisoquinoline could be synthesed from methyleugenol and acetonitrile in the presence sulphuric acid under reflux in 74,92% yields. In despite, the minor product was formed with amount 6,74%. While the reaction at room temperature gave dihydroisoquinoline in poor yield about 11,42%.


Keywords


stability of intermediate; dihydroisoquinoline; Ritter reaction

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References

[1] Lednicer, D., and Mitsher, L.A., 1990, The Organic Chemistry of Drug Synthesis, Volume III, p. 183, John Wiley & Sons Inc., New York.

[2] Fessenden, R.J., and Fessenden, J.S., 1990, Organic Chemistry, 4th ed., p. 250, 890, Cole Publishing Company, California.

[3] Chen, C.Y., Chang, F.R., Pan, W.B., and Wu, Y.C., 2001, Phytochem., 56, 753-757.

[4] Choi, K.B., Morishige, T., and Sato, F., 2001, Phytochem., 56, 649-655.

[5] Itoh, A., Tanahashi, T., and Nagakura, N., 1996, J. Nat. Prod., 59, 535-538.

[6] Fevig, T.L., Bowen, S.M., Janowick, D.A., Jones, B.K., Munson, H.R., Ohlweiler, D.F., and Thomas, C.E., 1996, J. Med. Chem., 39, 4988-4996.

[7] Watson, T.J.N., 1998, J. Org. Chem., 63, 406-407.

[8] Carrillo, L., Badia, D., Dominguez, E., Vicario, J.L., and Tellitu, I., 1997, J. Org. Chem., 62, 6716-6721.

[9] Grunewald, G.L., Dahanukar, V.H., Ching, P., and Criscione, K.R., 1996, J. Med. Chem., 39, 3539-3546.

[10] Farid, M.R., Matsjeh, S., and Soelistyowati, R.D., 2001, Synthesis of 1,3-Dimethyl-6,7-dimethoxy-3,4-dihydroisoquinoline via Ciclodehydration Reaction, Proceeding of International Seminar on Organic Chemistry, University of Gadjah Mada, Yogyakarta.

[11] Welniak, M., 2001, Polish J. Chem., 75, 55-62.

[12] Farid, M.R, 2002, Natural, 6 (2), 3-7.

[13] De Lijser, H.J.P. and Arnold, D.R., 1998, J. Phys. Chem. A, 102 (28), 5592-5598.

[14] March, J., 1992, Advanced Organic Chemistry ; Reactions, Mechanisms, and Structure, 4th ed., pp. 970-971 , John Wiley & Sons Inc., New York.

[15] Glushkov, V.A., Shurov, S.N., Maiorova, O.A., Postanogova, G.A., Feshina, E.V., and Shklyaef, Y.F., 2001, Chem. Heterocyclic Comp., 37(4), 444-452.

[16] Lambert, J.B., Shurvell, H.F., Lightner, D.A., and Cooks, R.G., 1998, Organic Structural Spectroscopy, pp. 201-242, Prentice-Hall Inc., New Jersey.

[17] Dyke, S.F., and Kinsman, R.G., 1981, Properties and Reactions of Isoquinolines and Their Hydrogenated Derivatives, p. 2, 11, John Wiley & Sons Inc., New York.

[18] Mc Lafferty, F.W., 1987, Interpretasi Spektra Massa, h. 292-293, terj. H. Sastrohamidjojo, Gadjah Mada University Press, Yogyakarta.



DOI: https://doi.org/10.22146/ijc.21733

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