| Summary: | 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.
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