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Sintesis senyawa 6-amino-2-( E)-2{( 4- metoksifenil) etenil}- 4(3h)- kuinazolinon = Synthesisof 6- amine- 2-{(- 4 metoxyphenyl ethenyl}-4 (3h) quinazolinone

Agung Budi Raharjo; Hayun, promotor; Arry Yanuar, co-promotor; Herman Suryadi, examiner; Harmita, examiner ([Publisher not identified] , 2014)

 Abstrak

[ABSTRAK
Perkembangan resistensi bakteri terhadap antibiotik menyebabkan perlunya
penelitian untuk menemukan senyawa baru yang memiliki aktivitas antibiotik.
Senyawa golongan kuinazolinon telah diketahui memiliki aktivitas sebagai
antibiotik. Oleh karena itu, dilakukan penelitian sintesis senyawa baru dari
golongan kuinazolinon dengan substitusi gugus stiril dan amin. Penelitian ini
bertujuan untuk memperoleh senyawa 6-amino-2-[(E)-2-(4-metoksifenil)etenil]-
4(3H)-kuinazolinon dan kondisi optimal yang dibutuhkan. Senyawa baru 6-
amino-2-[(E)-2-(4-metoksifenil)etenil]-4(3H)-kuinazolinon disintesis melalui
empat tahapan. Tahap pertama, sintesis 2-metil-4(3H)-kuinazolinon melalui reaksi
kondensasi antranilamida dengan asetamida dalam pelarut asam asetat glasial
dengan radiasi gelombang mikro. Tahap kedua, sintesis senyawa 2-metil-6-nitro-
4(3H)-kuinazolinon melalui reaksi nitrasi 2-metil-4(3H)-kuinazolinon dengan
asam nitrat berasap dan asam sulfat pekat pada suhu ruang. Tahap ketiga, sintesis
senyawa 6-nitro-2-[(E)-2-(4-metoksifenil)etenil]-4(3H)-kuinazolinon melalui
reaksi kondensasi antara p-metoksibenzaldehid dengan 2-metil-6-nitro-4(3H)-
kuinazolinon dalam pelarut asam asetat glasial dan natrium asetat anhidrat sebagai
dehydrating agent menggunakan radiasi gelombang mikro. Tahap keempat,
sintesis senyawa 6-amino-2-[(E)-2-(4-metoksifenil)etenil]-4(3H)-kuinazolinon
melalui reduksi senyawa 6-nitro-2-[(E)-2-(4-metoksifenil)etenil]-4(3H)-
kuinazolinon menggunakan serbuk besi dan HCl dalam pelarut methanol pada
suhu 45-550C dengan radiasi ultrasonik. Nilai rendemen tahap 1 90,19%, tahap 2
79,62%, tahap 3 63,93%, dan tahap 4 80,98%. Berdasarkan penelitian, senyawa
produk yang didapat pada setiap tahapan menunjukan struktur senyawa kimia
yang diharapkan. Struktur senyawa produk tahap 1 dan 2 dikonfirmasi
menggunakan metode spektroskopi IR, tahap 3 dan 4 menggunakan metode
spektroskopi UV-Vis, IR dan 1HNMR.

ABSTRACT
The growth of bacterial resistance to antibiotics led to the need for research to find
new compounds that have antibiotic activity. The class of quinazolinone
compounds known to have activity as an antibiotic. Therefore, research synthesis
of a new compound from the class of kuinazolinon by substituting stiril and amine
groups. This study aims to obtain compound 6-amino-2-[(E)-2-(4-methoxyphenyl)
ethenyl]-4(3H)-quinazolinone and optimal conditions required. The new
compound 6-amino-2-[(E)-2-(4-methoxyphenyl)ethenyl]-4(3H)-quinazolinone
synthesized through four steps. The first step is synthesis of 2-methyl-4(3H)-
quinazolinone through a condensation reaction between anthranilamide with
acetamide in glacial acetic acid using microwave irradiation. The second step is
synthesis of 2-methyl-6-nitro-4(3H)-quinazolinone through nitration reaction of 2-
methyl-4(3H)-quinazolinone using fuming nitric acid and concentrated sulfuric
acid at room temperature. The third step is synthesis 6-nitro-2-[(E)-2-(4-
methoxyphenyl)ethenyl]-4(3H)-quinazolinone through condensation reaction
between p-metoksibenzaldehid with 2-methyl-6-nitro-4(3H)-kuinazolinon in
glacial acetic acid and anhydrous sodium acetate as a dehydrating agent using
microwave irradiation. The fourth step is synthesis 6-amino-2-[(E)-2-(4-
methoxyphenyl)ethenyl]-4(3H)-kuinazolinon through reduction reaction of 6-
nitro-2-[(E)-2-(4-methoxyphenyl)ethenyl]-4(3H)-quinazolinone using iron powder
and hydrochloric acid in methanol at 45-550C with ultrasonic radiation. Yield
values obtained at each step 1, 2, 3, and 4 respectively are 90,19%, 79.62%,
63.93% and 80.98%. Based on the research, the product obtained at each stage
showed the expected chemical structure. The products structure of steps 1 and 2
were confirmed using IR spectroscopy methods, steps 3 and 4 were confirmed
using UV-Vis, IR and 1HNMR spectroscopy method., The growth of bacterial resistance to antibiotics led to the need for research to find
new compounds that have antibiotic activity. The class of quinazolinone
compounds known to have activity as an antibiotic. Therefore, research synthesis
of a new compound from the class of kuinazolinon by substituting stiril and amine
groups. This study aims to obtain compound 6-amino-2-[(E)-2-(4-methoxyphenyl)
ethenyl]-4(3H)-quinazolinone and optimal conditions required. The new
compound 6-amino-2-[(E)-2-(4-methoxyphenyl)ethenyl]-4(3H)-quinazolinone
synthesized through four steps. The first step is synthesis of 2-methyl-4(3H)-
quinazolinone through a condensation reaction between anthranilamide with
acetamide in glacial acetic acid using microwave irradiation. The second step is
synthesis of 2-methyl-6-nitro-4(3H)-quinazolinone through nitration reaction of 2-
methyl-4(3H)-quinazolinone using fuming nitric acid and concentrated sulfuric
acid at room temperature. The third step is synthesis 6-nitro-2-[(E)-2-(4-
methoxyphenyl)ethenyl]-4(3H)-quinazolinone through condensation reaction
between p-metoksibenzaldehid with 2-methyl-6-nitro-4(3H)-kuinazolinon in
glacial acetic acid and anhydrous sodium acetate as a dehydrating agent using
microwave irradiation. The fourth step is synthesis 6-amino-2-[(E)-2-(4-
methoxyphenyl)ethenyl]-4(3H)-kuinazolinon through reduction reaction of 6-
nitro-2-[(E)-2-(4-methoxyphenyl)ethenyl]-4(3H)-quinazolinone using iron powder
and hydrochloric acid in methanol at 45-550C with ultrasonic radiation. Yield
values obtained at each step 1, 2, 3, and 4 respectively are 90,19%, 79.62%,
63.93% and 80.98%. Based on the research, the product obtained at each stage
showed the expected chemical structure. The products structure of steps 1 and 2
were confirmed using IR spectroscopy methods, steps 3 and 4 were confirmed
using UV-Vis, IR and 1HNMR spectroscopy method.]

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 Metadata

Jenis Koleksi : UI - Skripsi Membership
No. Panggil : S55937
Entri utama-Nama orang :
Entri tambahan-Nama orang :
Entri tambahan-Nama badan :
Program Studi :
Subjek :
Penerbitan : [Place of publication not identified]: [Publisher not identified], 2014
Bahasa : ind
Sumber Pengatalogan : LibUI ind rda
Tipe Konten : text
Tipe Media : unmediated ; computer
Tipe Carrier : volume ; online resource
Deskripsi Fisik : xvi, 56 pages : illustration ; 30 cm + appendix
Naskah Ringkas :
Lembaga Pemilik : Universitas Indonesia
Lokasi : Perpustakaan UI, Lantai 3
  • Ketersediaan
  • Ulasan
  • Sampul
No. Panggil No. Barkod Ketersediaan
S55937 14-18-575362752 TERSEDIA
Ulasan:
Tidak ada ulasan pada koleksi ini: 20386691
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