Sintesis 2-(4-alil-2-metoksifenoksi)-N'-(1-benzil-2-oksoindolin-3-iliden)asetohidrazida

Roshuna, Jean Fitriani (2025) Sintesis 2-(4-alil-2-metoksifenoksi)-N'-(1-benzil-2-oksoindolin-3-iliden)asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Eugenol atau 4-alil-2 metoksifenol 1 merupakan salah satu senyawa fenil propanoid dalam kelompok aromatik alil benzena dengan gugus hidroksi, metoksi, dan alil menempel pada cincin benzena. Reaksi alkilasi eugenol pada gugus OH yang diikuti hidrazinolisis dengan hidrazin hidrat dapat memberikan senyawa 2-(4-alil-2-metoksifenoksi)asetohidrazida yang mengandung gugus hidrazida (-CONHNH2). Senyawa ini selanjutnya dapat mengalami substitusi dengan aldehida dan keton. Sementara itu, isatin yang mengandung gugus NH dan dua karbonil pada posisi C-2 dan C-3 dapat mengalami reaksi alkilasi, adisi nukleofilik, dan juga dapat bereaksi dengan amina primer dan sekunder. Penelitian ini bertujuan untuk melakukan sintesis senyawa 2-(4-alil-2-metoksifenoksi)-N’-(1-benzil-2-oksoindolin-3-iliden)asetohidrazida 35 melalui reaksi 2-(4-alil-2-metoksifenoksi)asetohidrazida 37 dengan 1-benzil indolin-2,3-dion 38. Penelitian ini diawali oleh alkilasi eugenol 1 dengan etil kloroasetat 41 menghasilkan etil 2-(4-alil-2-metoksifenoksi)asetat 36 dengan yield 98,04%. Hidrazinolisis senyawa 36 dengan hidrazin hidrat 42 memberikan senyawa 2-(4-alil-2-metoksifenoksi)asetohidrazida 37 (85,90% yield). Alkilasi juga dilakukan terhadap isatin 17 dengan benzil klorida 40 untuk memberikan 1-benzil indolin-2,3-dion 38 (85,75% yield). Reaksi 1-benzilindolin-2,3-dion 38 dengan 2-(4-alil-2 metoksifenoksi)asetohidrazida 37 selanjutnya berhasil memberikan 2-(4-alil-2-metoksifenoksi)-N’-(1-benzil-2-oksoindolin-3-iliden)asetohidrazida 35 dengan yield sebesar 26,43%.
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Eugenol or 4-allyl-2-methoxyphenol is a phenol derivative with the molecular formula C₁₀H₁₂O₂ and belongs to the allylbenzene aromatic compound group. Eugenol is a natural compound known for its strong pharmacological activities and can be chemically modified. This research aimed to synthesize a hybrid compound derived from eugenol and isatin derivatives, which is expected to exhibit biological activities such as anticancer, antioxidant, and antimicrobial effects. The target compound synthesized was 2-(4-allyl-2-methoxyphenoxy)-N'-(1-benzyl-2-oxoindolin-3-ylidene)acetohydrazide. The synthesis began with the alkylation of eugenol using ethyl chloroacetate to produce ethyl 2-(4-allyl-2-methoxyphenoxy)acetate with a yield of 98.4%, followed by amidation to form 2-(4-allyl-2-methoxyphenoxy)acetohydrazide with a yield of 85.90%. The isatin derivative was synthesized via alkylation with benzyl chloride to obtain 1-benzylindoline-2,3-dione with a yield of 85.83%. The final compound, 2-(4-allyl-2-methoxyphenoxy)-N'-(1-benzyl-2-oxoindolin-3-ylidene)acetohydrazide, was obtained by condensing 2-(4-allyl-2-methoxyphenoxy)acetohydrazide and 1-benzylindoline-2,3-dione, resulting in a yield of 26.43%.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Eugenol, Hidrazon, Isatin, Eugenol, Hydrazone, Isatin
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD481 Chemical structure.
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Jean Fitriani Roshuna
Date Deposited:	01 Aug 2025 07:33
Last Modified:	01 Aug 2025 07:33
URI:	http://repository.its.ac.id/id/eprint/125911

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