Nitric Acid → 1,4,7,8,9,10-Hexahydro-6-nitropyrido[3,4-f]quinoxaline-2,3-dione

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Reaction Steps

A solution of the quinoxalinedione from Example 30 (50 mg, 0.23 mmol) in 2 mL of trifluoroacetic acid was treated with fuming nitric acid (0.1 mL, 2.3 mmol) and stirred under a nitrogen atmosphere for 19 h. After evaporating to dryness, the residue was triturated with acetone and the precipitant collected by filtration. The solid was suspended in water, heated on a hot plate and basified to pH 8 with an ammonium hydroxide solution. The solid was collected by filtration while hot, and dried in vacuo to give a yellow solid (35 mg, 65% yield). mp=245-240° C. CHN calc'd for C11H10N4O4 found within theoretical limit ±0.4.

Provenance & Evidence