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

HRID 1106439Notes

Reaction equation

HRID 1106439 reaction equation
[NH:1]1[C:10]2[C:9]3[CH2:11][NH:12][CH2:13][CH2:14][C:8]=3[CH:7]=[CH:6][C:5]=2[NH:4][C:3](=[O:15])[C:2]1=[O:16].[N+:17]([O-])([OH:19])=[O:18]>FC(F)(F)C(O)=O>[N+:17]([C:7]1[C:8]2[CH2:14][CH2:13][NH:12][CH2:11][C:9]=2[C:10]2[NH:1][C:2](=[O:16])[C:3](=[O:15])[NH:4][C:5]=2[CH:6]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 212530731,4,7,8,9,10-Hexahydropyrido[3,4-f]quinoxaline-2,3-dione

Product 1

HCID 154347081,4,7,8,9,10-Hexahydro-6-nitropyrido[3,4-f]quinoxaline-2,3-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  1. customAfter evaporating to dryness
  2. customthe residue was triturated with acetone
  3. filtrationthe precipitant collected by filtration
  4. temperatureheated on a hot plate
  5. filtrationThe solid was collected by filtration while hot, and
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7ac75d7013b14d9f9aafb57a509a0fea
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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