Trifluoroacetic acid → HCID 10611559, compound

HRID 1857426Notes

Reaction equation

HRID 1857426 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][CH3:14])[NH:9][C:8](=[O:15])[C:7](=[O:16])[NH:6]2)[CH3:2].FC(F)(F)C(O)=O.[N+:24]([O-])([O-:26])=[O:25].[K+]>O>[N+:24]([C:11]1[C:12]([CH2:13][CH3:14])=[C:3]([CH2:1][CH3:2])[CH:4]=[C:5]2[C:10]=1[NH:9][C:8](=[O:15])[C:7](=[O:16])[NH:6]2)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24434Potassium NitrateHCID 10632607HCID 10632607, compound

Product 1

HCID 10611559HCID 10611559, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6,7-Diethyl-2,3-quinoxalinedione 25 (218 mg, 1.0 mmol) was added to trifluoroacetic acid (8 mL; Sigma). To this suspension was added potassium nitrate (121.2 mg, 1.2 mmol; Baker) in one portion with stirring under N2. The reaction was stirred at room temperature for 48 h. Trifluoroacetic acid was evaporated in vacuo to give a residue. Water (10 mL) was added to this residue with vigorous stirring. A yellow solid precipitated, which was collected by suction filtration and dried in vacuo to give 182 mg (69%) of the title compound 26 as a yellow solid; mp 270-272° C. (dec.); 1H NMR (DMSO-d6, 300 MHz) δ 1.137 (m, 6H), 2.622 (m, 4H), 7.088 (s, 1H), 11.762 (s, 1H), 12.028 (s, 11H). EIMS m/e 263 (100, M+). (HPLC purity 100%).

Workup

  1. stirringThe reaction was stirred at room temperature for 48 h
  2. customTrifluoroacetic acid was evaporated in vacuo
  3. customto give a residue
  4. customA yellow solid precipitated
  5. filtrationwhich was collected by suction filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4d38e57b948d46938ca15027718671ea
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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