1,2,4-Benzenetriamine, hydrochloride (1:2) → 2,3-Bis(3-hydroxyphenyl)quinoxalin-6-ylamine dihydrochloride salt

Participants

Reaction Steps

40.4 mg (0.206 mmol) of 1,2,4-benzenetriamine dihydrochloride and 50 mg (0.20 mmol) of 3,3′-dihydroxybenzil were dissolved in 2 mL of 1:1 mixture of dioxane-water. The reaction was refluxed for 3 hours. Then solvent was removed in vacuo. The residue was dissolved in 2 mL of methanol and this solution was added dropwise to 40 mL of diethyl ether. The formed dark-red precipitate was collected, washed with ether and dried in vacuo to give 69.8 mg (92.6% yield) of the product. 97.6% purity by LC/MS (230 DAD). Mass-spec [ES+]=330.8. 1H NMR (500 MHz, MeOH-d4) 6.81–6.87 (2H, m), 6.96–6.98 (4H, m), 7.10 (1H, m), 7.13–7.16 (1H, t), 7.28–7.31 (1H, t), 7.56–7.58 (1H, m), 8.04–8.06 (1H, d).

Provenance & Evidence