Reaksi 2-(4-Alil-2-metoksifenoksi)asetohidrazida dengan Isatin dan 5-Metilisatin

Niadisti, Bella Ratih Apsari (2025) Reaksi 2-(4-Alil-2-metoksifenoksi)asetohidrazida dengan Isatin dan 5-Metilisatin. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Eugenol 1 merupakan senyawa fenil propanoid tipe alil-fenol dengan satu gugus aromatik cincin benzena dan tiga substituen berupa hidroksil (-OH), metoksi (-OCH3), dan rantai alil (H2C=CH-CH2), dapat dimodifikasi melalui reaksi alkilasi, asetilasi, dan asilasi. Senyawa hidrazida dengan gugus azometin (-CONHNH2) dapat diperoleh melalui reaksi hasil alkilasi eugenol dengan hidrazin hidrat dan dapat bereaksi lebih lanjut dengan berbagai elektrofil seperti aldehida, keton, dan asil klorida. Isatin 6 merupakan senyawa heterosiklik golongan indola yang mengandung dua gugus karbonil pada posisi C2 dan C3 yang dapat mengalami reaksi adisi nukleofilik pada karbonil C3. Studi literatur mengungkap bahwa isatin 6 dapat bereaksi dengan senyawa hidrazida. Penelitian ini bertujuan untuk melakukan reaksi antara senyawa eugenol hidrazida berupa 2-(4-alil-2-metoksifenoksi)asetohidrazida 5 dengan isatin 6a dan 5-metilisatin 6b. Penelitian diawali dengan reaksi alkilasi eugenol 1 melalui reaksi substitusi gugus hidroksi eugenol 1 oleh etil kloroasetat 2 dalam DMF dengan penambahan kalium karbonat yang memberikan etil 2-(4-alil-2-metoksifenoksi)asetat 3 (98,46% yield). Hidrazinolisis lebih lanjut senyawa 3 dengan hidrazin hidrat 4 dalam etanol menghasilkan 2-(4-alil-2 metoksifenoksi)asetohidrazida 5 dengan yield 88,07%. Reaksi senyawa 5 dengan isatin 6a dan 5-metilisatin 6b akhirnya berhasil memberikan senyawa eugenol dengan motif isatin berupa 2-(4-alil-2-metoksifenoksi)-N'-(2-oksoindolin-3-iliden)asetohidrazida 7a dan 2-(4-alil-2-metoksifenoksi)-N'-(5-metil-2-oksoindolin-3-iliden)asetohidrazida 7b masing-masing dengan yield sebesar 84,38% dan 80,15%. Spektrometer FTIR, NMR, dan analisis massa digunakan untuk menetapkan struktur senyawa hasil sintesis.

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Eugenol 1 is an allyl-phenol type phenyl propanoid compound with one aromatic benzene ring group and three substituents in the form of hydroxyl (-OH), methoxy (-OCH3), and allyl chain (H2C=CH-CH2), which can be modified through alkylation, acetylation, and acylation reactions. Hydrazide compounds with azomethine groups (-CONHNH2) can be obtained through the alkylation reaction of eugenol with hydrazine hydrate and can further react with various electrophiles such as aldehydes, ketones, and acyl chlorides. Isatin 6 is a heterocyclic compound of the indole group containing two carbonyl groups at positions C2 and C3 that can undergo nucleophilic addition reactions at the C3 carbonyl. Literature studies reveal that isatin 6 can react with hydrazide compounds. This study aims to conduct a reaction between the eugenol hydrazide compound 2-(4-allyl-2-methoxyphenoxy)acetohydrazide 5 with isatin 6a and 5-methylisatin 6b. The study began with the alkylation of eugenol 1 through the substitution of the hydroxy group of eugenol 1 by ethyl chloroacetate 2 in DMF with the addition of potassium carbonate, yielding ethyl 2-(4-allyl-2-methoxyphenoxy)acetate 3 (98.46% yield). Further hydrazinolysis of compound 3 with hydrazine hydrate 4 in ethanol yielded 2-(4-allyl-2-methoxyphenoxy)acetohydrazide 5 with a yield of 88.07%. The reaction of compound 5 with isatin 6a and 5-methylisatin 6b finally yielded eugenol with an isatin motif in the form of 2-(4-allyl-2-methoxyphenoxy)-N'-(2-oxoindolin-3-ylidene)acetohydrazide 7a and 2-(4-allyl-2-methoxyphenoxy)-N'-(5-methyl-2-oxoindolin-3-ylidene)acetohydrazide 7b, respectively, with yields of 84.38% and 80.15%. FTIR spectrometer, NMR, and mass analysis were used to determine the structure of the synthesized result.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Eugenol, isatin, 5-metilisatin, sintesis, spektrometer, 5-methylisatin, synthesis, spectrometer
Subjects:	Q Science Q Science > QD Chemistry > QD1 Oxidation-reduction reaction. Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas Q Science > QD Chemistry > QD75.2 Chemistry, Analytic
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Bella Ratih Apsari Niadisti
Date Deposited:	04 Aug 2025 08:10
Last Modified:	04 Aug 2025 08:10
URI:	http://repository.its.ac.id/id/eprint/126455

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