Sintesis N'-(4-Hidroksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida

Hidayati, Adinda Fitria (2023) Sintesis N'-(4-Hidroksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Kumarin termasuk senyawa heterosiklik sederhana golongan benzopiron (benzo-α-piron). Perubahan struktur dasar pada kumarin berpengaruh terhadap aktivitas biologisnya. Modifikasi struktur kumarin dapat dilakukan dengan penambahan gugus farmakofor pada posisi C-3, C-4 dan C-7. Senyawa 7-hidroksi-4-metilkumarin 6 merupakan salah satu turunan dari kumarin yang dapat dimodifikasi melalui alkilasi, penambahan gugus amina, dan substitusi dengan aldehida. Modifikasi ini dilaporkan mampu meningkatkan aktivitas biologis senyawa hasil sintesis. Penelitian yang dilakukan bertujuan untuk mendapatkan N'-(4-hidroksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 1. Penelitian yang dilakukan telah berhasil mendapatkan 7-hidroksi-4-metilkumarin 6 dengan rendemen 63,82%. Alkilasi 7-hidroksi-4-metilkumarin 6 dengan etil kloroasetat 7 dan penambahan basa kalium karbonat memberikan etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dengan rendemen 57,40%. Selanjutnya, reaksi antara etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dengan hidrazin hidrat 5 menghasilkan produk 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 dengan rendemen 94,86%. Reaksi 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 dengan 4-hidroksibenzaldehida 3 dalam suasana asam memberikan N'-(4-hidroksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 1 dengan rendemen 97,90%.

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Coumarins are simple heterocyclic compounds of the benzopyrone (benzo-α-pyrone) group. Changes in the basic structure of coumarins affect their biological activity. Modification of coumarin structure can be done by adding pharmacophore groups at C-3, C-4 and C-7 positions. The 7-hydroxy-4-methylcoumarin 6 compound is a derivative of coumarin which can be modified through alkylation, addition of amine groups, and substitution with aldehydes. This modification is reported to increase the biological activity of the synthesized compounds. The purpose of the research was to obtain N'-(4-hydroxybenzylidene)-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 1. The research was successful in obtaining 7-hydroxy- 4-methylcoumarin 6 with a yield of 63.82%. Alkylation of 7-hydroxy-4-methylcoumarin 6 with ethyl chloroacetate 7 and addition of base potassium carbonate gives ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 with a yield of 57.40% . Furthermore, the reaction between ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 and hydrazine hydrate 5 produces the product 2-((4-methyl-2-oxo-2H-chromen -7-yl)oxy)acetohydrazide 2 in 94.86% yield. The reaction of 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 2 with 4-hydroxybenzaldehyde 3 in an acidic condition gives N'-(4-hydroxybenzylidene)-2-((4-methyl -2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 1 in 97.90% yield.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	coumarin, 7-hydroxy-4-methylcoumarin, 4-hydroxybenzaldehyde, benzylidene, kumarin, 7-hidroksi-4-metilkumarin, 4-hidroksibenzaldehida, benzilidena
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Adinda Fitria Hidayati
Date Deposited:	17 Feb 2023 08:42
Last Modified:	17 Feb 2023 08:42
URI:	http://repository.its.ac.id/id/eprint/97469

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