Indonesian Journal of Chemistry
Vol 4, No 2 (2004)

SYNTHESIS OF ANTIMALARIAL 3-(2-HYDROXYETHYL)-2-METHYL-1,10-PHENANTHROLINE-4-OL FROM 8-AMINOQUINOLINE

Ruslin Hadanu (Chemistry Department, Pattimura University, Ambon)
Chairil Anwar (Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281)
Jumina Jumina (Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281)
Iqmal Tahir (Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281)
Mustofa Mustofa (Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta 55281)



Article Info

Publish Date
09 Jun 2010

Abstract

It has been conducted the synthesis of 3-(2-hydroxyethyl)-2-methyl-1,10-phenanthroline-4-ol was carried out from 8-aminoquinoline which are expected to posses antimalarial activity. The experiment perfomed consisted of two steps i.e (1) reaction of 8-aminoquinoline with 2-acetyl-butyrolactone and (2) cyclization of the resulted 3-[1-(quinolin-8-ylamino)-ethylidene]-4,5-dihydro-furan-2-one. The reaction of 8-aminoquinoline with 2-acetyl-butyrolactone was performed in toluene at reflux for 6 hours in the presence of p-toluensulfonic acid as catalyst. This reaction gave 3-[1-(quinolin-8-ilamino)-etiliden]-4,5-dihidro-furan-2-on in 60.6% yield. The cyclization of 3-[1-(quinoline-8-ylamino)-ethyliden]-4,5-dihydro-furan-2-one was conducted in cloroform at reflux for 4 hours in the presence of H2SO4 as catalyst and also tween 80 as transfer phase catalyst to give 3-(2-hydroxy-ethyl)-2-methyl-1,10-phenanthroline-4-ol in 76.2% yield. Identification of the products were carried out by means of infra red (IR) spectroscopy, proton nuclear magnetic resonance (1H-NMR) spectroscopy, and mass spectroscopy (MS).

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Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...