Uses
Degradation of Acid Black 1 reveals the formation of 3-Aminocatechol as one of the intermediates.
Synthesis
2,3-Dimethoxyaniline (438 μL, 3.26 mmol) was used as raw material and dissolved in dichloromethane (5.0 mL). A 1 mol/L solution of boron tribromide/dichloromethane (11.4 mL, 11.4 mmol) was slowly added dropwise at -78 °C under argon protection. After the dropwise addition, the reaction system was slowly warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium bicarbonate solution and subsequently neutralized with saturated aqueous ammonium chloride solution. The reaction mixture was extracted with ethyl acetate and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford the target product 3-aminobenzene-1,2-diol (67 mg, 16% yield).
IC 50
MMP-2: 20 μM (IC
50); MMP-8: 26 μM (IC
50); MMP-9: 16 μM (IC
50); MMP-14: 16.3 μM (IC
50)
References
[1] Patent: JP2016/124812, 2016, A. Location in patent: Paragraph 0098
[2] Patent: US2003/65018, 2003, A1
[3] Patent: WO2007/71434, 2007, A1. Location in patent: Page/Page column 60-61
