SINTESIS 3-BENZILIDEN-2-BUTILISOINDOLINON BERBAHAN DASAR BUTILAMINA MELALUI REAKSI ONE-POT

IFADATINNIDA, Dr. Muhammad Idham Darussalam M, M.Sc.

2019 | Skripsi | S1 KIMIA

Sintesis 3-benziliden-2-butilisoindolinon dari bahan dasar butilamina melalui reaksi one-pot telah dilakukan. Tujuan peneliti an ini adalah untuk mensintesis 3-benzilidenftalida melalui kopling Sonogashira, mensintesis 3-benziliden-2-butilisoindolinon melalui reaksi dua tahap yaitu reaksi adisi nukleofilik dan beta-eliminasi. Selain itu, penelitian ini juga bertujuan mensintesis 3-benziliden-2-butilisoindolinon melalui reaksi one-pot yang menggabungkan reaksi adisi nukleofilik dan beta-eliminasi. Tahap pertama adalah mensintesis3-benzilidenftalida dengan mereaksikan fenilasetilena dengan asam 2-iodobenzoat dalam pelarut DMSO dengan adanya katalis CuI dan basa NaHCO3 pada temperatur ruang selama 24 jam. Selanjutnya, ftalida direaksikan dengan butilamina pada suhu 50 oC selama 6 jam melalui reaksi adisi nukleofilik. Senyawa 3-benzil-2-butil-hidroksiisoindolinon yang didapatkan ditambahkan katalis HCl 6 M kemudian dipanaskan pada suhu 50 oC selama 3 jam melalui reaksi beta-eliminasi. Selain itu, sintesis 3-benziliden-2-butilisoindolinon juga dilakukan melalui reaksi one-pot yang menggabungkan reaksi adisi nukleofilik dan beta-eliminasi. Produk sintesis dikarakterisasi dengan spektrometer 1H-NMR, 13C-NMR dan FTIR serta diuji titik lebur. Reaksi Sonogashira antara asam 2-iodobenzoat dan fenilasetilena menghasilkan 3-benzilidenftalida dengan persen hasil 64%. Reaksi adisi nukleofilik antara 3-benzilidenftalida dan butilamina menghasilkan 3-benzil-2-butil-3-hidroksiisoindolinon dengan persen hasil 82%. Reaksi beta-eliminasi antra 3-benzil-2-butil-3-hidroksiisoindolinon terkatalisis HCl menghasilkan 3-benziliden-2-butilisoindolinon dengan persen hasil sebesar 67%. Reaksi one-pot antara 3-benzilidenftalida dan butilamina menghasilkan 3-benziliden-2-butilisoindolinon dengan persen hasil 87%. Berdasarkan perbandingan persen hasil antara reaksi dua tahap dan reaksi one-pot, maka reaksi one-pot lebih efektif, efisien dan ramah lingkungan.

Synthesis of 3-benzylden-2-butylisoindolinone via one-pot reaction has been conducted. The research was aimed to synthesize 3-benzylidenphtalide via Sonogashira coupling using phenylacetylene and 2-iodobenzoic acid, to synthesize 3-benzyliden-2-butylisoindolinone from 3-benzylidenphtalide and butylamine via two- step reactions consisting of a nucleophilic addition reaction and beta-elimination. In addition, this study was also aimed to synthesize 3-benzyliden-2-butylisoindolinone via one-pot reaction, which combines nucleophilic addition reaction and beta-elimination. The first step was to synthesize 3-benzylidenphtalide via the Sonogashira reaction by reacting phenylacetylene and 2-iodobenzoic acid for 24 hours in the presence of CuI catalyst and NaHCO3 as base at room temperature. Furthermore, the phthalide was reacted with butylamine at 50 oC for 6 hours via nucleophilic addition reactions. The 3-benzyl-2-butyl-hydroxyisoindolinone obtained was added with HCl 6 M as catalyst, then heated at 50 oC for 2 hours via beta-elimination reaction. In addition, synthesis of 3-benzyliden-2-butylisoindolinone was also carried out via a one-pot reaction which combines nucleophilic addition reaction and beta-elimination. The products were characterized by 1H-NMR, 13C-NMR, FTIR spectrometers and melting point test. The Sonogashira reaction between 2-iodobenzoic acid and phenylacetylene produced 3-benzilidenphtalide in 64% yield. The nucleophilic addition reaction between 3-benzlidenphtalide and butylamine generated 3-benzyl-2-butyl-3-hidroxyisoindolinone in 82% yield. The beta-elimination reaction of 3-benzyl-2-butyl-3-hidroxyisoindolinone, in the presence of HCl catalyst, gave 3-benzyliden-2-butylisoindolinone in 67% yield. A one-pot reaction between 3-benzylidenphtalide and butylamine produced 3-benzyliden-2-butylisoindolinone in 87% yield. By comparing the yield of reaction, one-pot reaction is more effective, efficient and environmentally friendly.

Kata Kunci : reaksi one-pot, benzilidenisoindolinon, adisi nukleofilik, beta-eliminasi, Sonogashira