Nitric Acid → HCID 18369254, compound

HRID 1699723Notes

Reaction equation

HRID 1699723 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[NH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].[N+:18]([O-])([OH:20])=[O:19]>C(O)(=O)C>[CH3:17][C:10]1[CH:9]=[C:8]2[C:13]([NH:14][C:15](=[O:16])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:7]2)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18008890HCID 18008890, compound

Product 1

HCID 18369254HCID 18369254, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl-3,4-dihydro-7-methyl-3-oxoquinoxaline-2-carboxylate (1.65 g, 7.10 mmol) in acetic acid (15 ml) was added dropwise fuming nitric acid (1.36 ml, 14.2 mmol), and the mixture was stirred for 1 hour at 60° C. The reaction mixture was poured into ice water and, after stirring for 25 minutes, the precipitate was collected by filtration. These were air-dried and then dissolved into ethyl acetate. Moreover, the filtrate was extracted with ethyl acetate, which was combined with foregoing organic layer. After dried over anhydrous sodium sulfate, solvent was distilled off. The residue obtained was purified by means of silica gel column chromatography [n-hexane:ethyl acetate=1:1] to obtain 887 mg of the title compound as pale yellow powder. Yield 45%.

Workup

  1. stirringafter stirring for 25 minutes
  2. filtrationthe precipitate was collected by filtration
  3. customThese were air-dried
  4. dissolutiondissolved into ethyl acetate
  5. extractionMoreover, the filtrate was extracted with ethyl acetate, which
  6. dry with materialAfter dried over anhydrous sodium sulfate, solvent
  7. distillationwas distilled off
  8. customThe residue obtained
  9. customwas purified by means of silica gel column chromatography [n-hexane:ethyl acetate=1:1]

Sources & evidence

ORD record
ord-02ef1f99e1494245b63ab673007be363
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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