SINTESIS 1-BENZIL-3-METIL-6,7-DIMETOKSI-3,4-DIHIDROISOKUINOLINA DARI METILEUGENOL

• Main Authors: , NOVA RIFATUL ULYA, , Prof. Drs. Sabirin Matsjeh, Ph.D.
• Format: Theses and Dissertations NonPeerReviewed
• Published: [Yogyakarta] : Universitas Gadjah Mada 2013
• Subjects: ETD
• Online Access: https://repository.ugm.ac.id/119389/; http://etd.ugm.ac.id/index.php?mod=penelitian_detail&sub=PenelitianDetail&act=view&typ=html&buku_id=59387
• Institution: Universitas Gadjah Mada

A synthesis of 1-benzyl-3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline from methyleugenol as starting material is presented. The synthesis was carried out several reactions steps, these are addition reactions, hydrolysis, Ritter reaction and cyclization. The compound of 1-benzyl-3-methyl-6,7-dimethoxy-3,4- dihydroisoquinoline is isoquinoline derivative that have potential as drug compound. The synthesis of 1-benzyl-3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline from methyleugenol has been achieved through conversion of allyl group to secondary alcohol, followed by Ritter reaction with benzyl cyanide and cyclization reaction with sulfuric acid. The secondary alcohol has been achieved by two methods. The first method was formic acid addition reaction, and then the second method was hydrolysis in solution of potassium hydroxide. The next reaction was the Ritter reaction of the secondary alcohol and the last method was the cyclization reaction of amide to isoquinoline. The addition reaction of methyleugenol with formic acid yield 1-(3,4- dimethoxyphenyl)-2-propyl formate (86,46%). The hydrolysis of 1-(3,4- dimethoxyphenyl)-2-propyl formate with KOH produced 1-(3,4-dimethoxyphenyl)-2- propanol (86,41%). The Ritter reaction of 1-(3,4-dimethoxyphenyl)-2-propanol with benzyl cyanide gave (34,70%) N-[1-methyl-2-(3,4-dimethoxyphenyl)ethyl]-2-phenyl acetamide. And the last reaction is cyclization with sulfuric acid gave 1-benzyl-3- methyl-6,7-dimethoxy-3,4-dihydroisoquinoline as a main target in 39%. The structure elucidation of these product were analyzed by FTIR,1H-NMR, and GC-MS.