Gemilang Hardyanputrinda and Juni Ekowati and Marcellino Rudyanto (2015) Pengaruh substituen 2-metoksi pada sintesis turunan 2-hidroksibenzohidrazida dengan iradiasi gelombang mikro. Berkala Ilmiah Kimia Farmasi, 4 (2). pp. 5-10. ISSN 2302-8270

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Abstract

N’-benzylidene-2-hydroxybenzohydrazide and N’-(2-methoxybenzylidene)-2-hydroxybenzo-hydrazide are hydrazide derived compounds that could be made from methyl salicylate. The aim of this research is to determine the influence of methoxy substituent on ortho position in the synthesis of N’-(2-methoxybenzylidene)-2-hydroxybenzohydrazide through the yields of synthesis comparisons with N’-benzylidene-2-hydroxybenzohydrazide by microwave irradiation. N’-(2-methoxy-benzylidene)-2-hydroxybenzohydrazide synthesized from structure modification of methyl salicylate through 2 phases of reaction, nucleophilic acyl substitution to produce 2-hydroxybenzohydrazide and nucleophilic addition to produce target compound. Methoxy group influences carbonyl reactivity through resonance and steric effect in nucleophilic addition. N’-benzylidene-2-hydroxybenzohydrazide is white, needle-shaped crystal (88 ± 2.5)% and N’-(2-methoxybenzylidene)-2-hydroxybenzohydrazide is white round solids (76 ± 3.5)%. Concluded that o-methoxy substitutient decrease carbonyl reactivity in nucleophilic addition of N’-(2-methoxybenzylidene)-2-hydroxybenzohydrazide synthesis.

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