Chemical Properties
Dark Brownish Black Solid
Uses
4-Methoxy-o-phenylenediamine is widely used as an intermediate in organic synthesis and pharmaceuticals. It is an important precursor for the synthesis of other heterocyclic compounds. It is used in the determination of glyoxal, methylglyoxal, and diacetyl in urine using 4-methoxy-o-phenylenediamine as a derivatizing reagent by High-performance liquid chromatography (HPLC).
Synthesis
General procedure for the synthesis of 4-methoxy-o-phenylenediamine from 4-methoxy-2-nitroaniline: 360 mg (2.14 mmol) of 4-methoxy-2-nitroaniline was placed in a hydrogenation reactor and 65 mL of ethanol was added. Subsequently, a small amount of 10% palladium/activated carbon catalyst was added and the reaction mixture was hydrogenated at room temperature under 50 Psi hydrogen pressure for 24 hours. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated on a rotary evaporator to afford 4-methoxyphthalimide (294 mg, 2.12 mmol, 99% yield) as a dark purple oil. The product was characterized by 1HNMR (CDCl3): δ 6.64 (d, J = 8.7 Hz, 1H), 6.35-6.30 (m, 1H), 6.26 (d, J = 8.7 Hz, 1H), 3.52 (s br, 2H), 3.07 (s br, 2H).
References
[1] Patent: US2013/315825, 2013, A1. Location in patent: Paragraph 0220
[2] Patent: WO2010/84152, 2010, A1. Location in patent: Page/Page column 109-110
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 7, p. 1756 - 1758
[4] RSC Advances, 2015, vol. 5, # 78, p. 63421 - 63428
[5] Patent: WO2017/37604, 2017, A1. Location in patent: Page/Page column 25
