Sintesis Etil (E)-2-(3-(2-(2-(4-Formil-2-Metoksifenoksi)Asetil)Hidraziniliden)-2-Oxoindolin-1-il)Asetat

Oktafiana, Ellisa (2024) Sintesis Etil (E)-2-(3-(2-(2-(4-Formil-2-Metoksifenoksi)Asetil)Hidraziniliden)-2-Oxoindolin-1-il)Asetat. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Vanilin 8 (4-hidroksi-3-metoksibenzaldehida), merupakan aldehida fenolik dengan gugus fungsi aldehida, hidroksil, dan eter. Vanilin 8 memiliki beberapa bioaktivitas, antara lain antitumor, antimetastatik, antimikroba, antijamur, antiinflamasi, antioksidan, dan antivirus. Isatin 4 mempunyai posisi serba guna, dimana banyak reaksi dapat terjadi sehingga mampu membentuk produk dengan vanilin 8. Penelitian ini dilakukan untuk memperoleh turunan vanilin 8 dengan substituen isatin 4 berupa etil (E)-2-(3-(2-(2-(4-formil-2-metoksifenoksi)asetil)hidraziniliden)-2-oxoindolin-1-il)asetat 1. Sintesis senyawa 1 dilakukan melalui reaksi substitusi gugus hidroksi vanilin 8 oleh etil kloroasetat 5 menghasilkan etil 2-(4-formil-2-metoksifenoksi)asetat 6 dengan %yield 67%. Reaksi senyawa 6 selanjutnya dengan hidrazin hidrat 7 memberikan 2-(4-formil-2-metoksifenoksi)asetohidrazida 2 dengan %yield 91%. Reaksi alkilasi antara isatin 4 dan etil kloroasetat 5 memberikan senyawa etil 2-(2,3-dioxoindolin-1-il)asetat 3 dengan %yield 75%. Reaksi antara senyawa 2 dan 3 menghasilkan etil (E)-2-(3-(2-(2-(4-formil-2-metoksifenoksi)asetil)hidraziniliden)-2-oxoindolin-1-il)asetat 1 dengan %yield sebesar 71%.
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Vanillin 8 (4-hydroxy-3-methoxybenzaldehyde), is a phenolic aldehyde with aldehyde, hydroxyl and ether functional groups. Vanillin 8 has several bioactivities, including antitumor, antimetastatic, antimicrobial, antifungal, anti-inflammatory, antioxidant and antiviral. Isatin 4 has a versatile position, where many reactions can occur so that it can form products with vanillin 8. This research was carried out to obtain vanillin 8 derivatives with isatin 4 substituents in the form of ethyl (E)-2-(3-(2-(2-( 4-formyl-2-methoxyphenoxy)acetyl)hydrazineylidene)-2-oxoindolin-1-yl)acetate 1. Synthesis of compound 1 was carried out through a substitution reaction for the hydroxy group of vanillin 8 by ethyl chloroacetate 5 to produce ethyl 2-(4-formyl-2-methoxyphenoxy)acetate 6 with a yield of 67%. The subsequent reaction of compound 6 with hydrazine hydrate 7 gave 2-(4-Formyl-2-methoxyphenoxy)acetohydrazide 2 with a yield of 91%. The alkylation reaction between isatin 4 and ethyl chloroacetate 5 gave the compound ethyl 2-(2,3-dioxoindolin-1-yl)acetate 3 with a yield of 75%. The reaction between compounds 2 and 3 produces ethyl (E)-2-(3-(2-(2-(4-formyl-2-methoxyphenoxy)acetyl)hydrazineylidene)-2-oxoindolin-1-yl)acetate 1 with %yield amounting to 71%.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	vanilin, isatin, alkilasi, benzilidena. vanillin, isatin, alkylation, benylidene.
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:	Ellisa Oktafiana
Date Deposited:	14 Aug 2024 01:59
Last Modified:	14 Aug 2024 01:59
URI:	http://repository.its.ac.id/id/eprint/114250

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