Alloxan → 1,2,3,4-Tetrahydrobenzopteridine-2,4-dione

Participants

Reaction Steps

There was charged 800 ml of water into an Erlenmeyer flask, then 3.5 g (30 mmoles) of o-phenylenediamine and 5.0 g (30 mmoles) of alloxan were added thereto, and the mixture was stirred at room temperature in a nitrogen atmosphere for about 5 hours. The obtained reaction mixture was cooled with ice for 3 hours, then the formed yellow precipitate was filtered off, and washed in ethanol and ether (50 ml, twice). This precipitate was recrystallized from an aqueous dimethylformamide solution to give pale yellow powdery crystals. Yield: 7.5 g (90%). M.p. 300° C. or higher. IR spectrum: Found values (cm-1): 1730, 1705 (C=O stretching), 1572 (Broad peak) --C=N (amide II band). Literature values (cm-1): 1727, 1700, 1574.

Provenance & Evidence