Chemical Properties
Methyl 4-amino-3-nitrobenzoate is a synthetic compound that has been found to have a variety of uses. It has been used to prepare intramolecular hydrogen bonds in anilines, and it can be used as an intermediate to synthesize amides and anilines. This molecule also forms resonance structures with the nitro group, which allows for increased stability. The proton magnetic resonance spectra of Methyl 4-amino-3-nitrobenzoate show that the molecule has a high degree of symmetry, which is due to the presence of intramolecular hydrogen bonding.
Synthesis
4-Amino-3-nitrobenzoic acid (50 g, 270 mmol, 1 eq.) was suspended in methanol (600 mL) at room temperature. Subsequently, sulfoxide chloride (20 mL, 270 mmol, 1 eq.) was slowly added dropwise to the above suspension. The reaction mixture was heated to reflux for 16 h. After completion of the reaction, it was cooled to room temperature. The resulting yellow solid, methyl 4-amino-3-nitrobenzoate (D1) (53 g, 100% yield), was collected by filtration, and the product could be used in subsequent reactions without further purification. Mass spectrometry analysis showed [M + H]+ = 197.3, retention time (RT) = 2.42 min.
References
[1] Patent: WO2004/94430, 2004, A1. Location in patent: Page 16
[2] Patent: WO2006/40148, 2006, A1. Location in patent: Page/Page column 19-20
[3] Patent: WO2015/57938, 2015, A1. Location in patent: Page/Page column 102
[4] Patent: CN106146416, 2016, A. Location in patent: Paragraph 0046; 0047; 0048; 0049; 0050
[5] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 8 - 20
