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

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

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Abstract

Kumarin 1 merupakan senyawa organik heterosiklik golongan fenilpropanoid dengan cincin lakton lingkar enam dan banyak ditemukan pada berbagai jenis tanaman. Kumarin 1 dan berbagai turunannya menunjukkan berbagai aktivitas farmakologis. Senyawa 4-metilumbelliferona 10 dengan kerangka kumarin telah digunakan sebagai obat untuk meredakan kejang dan otot. Modifikasi struktur 4-metilumbelliferona 10 dapat dilakukan dengan pembentukan kerangka benzilidena dalam strukturnya. Senyawa yang mengandung benzilidena dilaporkan memiliki sifat biologis yang baik. Penelitian yang dilakukan bertujuan untuk mendapatkan N’-(2-hidroksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)ase-tohidrazida 19 melalui modifikasi 4-metilumbelliferona 10. Penelitian dilakukan melalui sintesis 4-metilumbelliferona 10, etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 23, dan 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 21 yang dilanjutkan dengan substitusi 2-hidroksibenzaldehida 20. Penelitian yang dilakukan telah berhasil mendapatkan 4-metilumbelliferona 10 dengan rendemen 63,82% melalui reaksi kondensasi resorcinol 25 dengan etil asetoasetat 26. Etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 23 dengan rendemen 57,40% telah diperoleh melalui alkilasi 4-metilumbelliferona 10 dengan kalium karbonat dan etil kloroasetat 24. Berikutnya, 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 21 dengan rendemen 94,86% diperoleh melalui reaksi antara etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 23 dengan hidrazin hidrat 22. Akhirnya, N’-(2-hidroksibenzilidena)-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 19 dengan rendemen sebesar 78,37% telah berhasil diperoleh melalui reaksi 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 21 dengan 2-hidroksibenzaldehida 20 dalam suasana asam.
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Coumarins 1 are heterocyclic organic compounds of the phenylpropanoid group with a six-ring lactone ring and are found in many types of plants. Coumarins 1 and their various derivatives exhibit a wide range of pharmacological activities. The compound 4-metilumbelliferone 10 with a coumarin framework has been used as a drug to relieve spasms and muscle spasms. Modification of the structure of 4-methylumbelliferone 10 can be carried out by forming a benzylidene framework in its structure. Compounds containing benzylidene are reported to have good biological properties. The aim of the research was to obtain N'-(2-hydroxybenzylidene)-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydra-zide 19 through modification of 4-methylumbelliferone 10. The research was conducted via the synthesis of 4-methylumbelliferone 10, ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 23, and 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 21 followed by substitution of 2-hydroxybenzaldehyde 20. The research has succeeded in obtaining 4-methylumbelliferone 10 with a yield of 63.82% through the condensation reaction of resorcinol 25 with ethyl acetoacetate 26. Ethyl 2-((4- methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 23 in a yield of 57.40% was obtained by alkylation of 4-methylumbelliferone 10 with potassium carbonate and ethyl chloroacetate 24. Next, 2-((4-methyl- 2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 21 with a yield of 94.86% was obtained by the reaction between ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 23 with hydrazine hydrate 22. Finally, N'-(2-hydroxybenzylidene)-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 19 with a yield of 78.37% has been successfully obtained through the reaction of 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 21 with 2-hydroxybenzaldehyde 20 in acidic condition.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	kumarin, 4-metilumbelliferona, 2-hidroksibenzaldehida, benzilidena, coumarin, 4-methylumbelliferone, 2-hidroxybenzaldehyde, benzylidene
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:	Reynal Restu Affandi
Date Deposited:	17 Feb 2023 10:39
Last Modified:	17 Feb 2023 10:39
URI:	http://repository.its.ac.id/id/eprint/97468

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