Synthesis
General procedure for the synthesis of 2-amino-4,5-dimethoxybenzaldehyde from 4,5-dimethoxy-2-nitrobenzaldehyde: Pd/C catalyst (5%, 0.5 g) was suspended in a solution of 4,5-dimethoxy-2-nitrobenzaldehyde (3.1 g, 4.74 mmol) in anhydrous THF (10 mL). The reaction mixture was subjected to a hydrogen atmosphere at 50 psi pressure for 15 minutes at room temperature with stirring. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography to afford the target product 2-amino-4,5-dimethoxybenzaldehyde (0.85 g, 99% yield).
References
[1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 8, p. 2480 - 2486
[2] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 413 - 423
[3] Tetrahedron Letters, 2015, vol. 56, # 25, p. 3954 - 3960
[4] Patent: JP2018/52878, 2018, A. Location in patent: Paragraph 0149
[5] Canadian Journal of Chemistry, 2004, vol. 82, # 3, p. 461 - 478
