Toluene → HCID 18369162, compound

HRID 1699734Notes

Reaction equation

HRID 1699734 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)[N:4]=[C:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[N+:21]([O-:24])([O-])=[O:22].[K+].[C:26]1(C)C=CC=C[CH:27]=1.ICC>S(=O)(=O)(O)O.[Ag]=O.CCCCCC.C(OCC)(=O)C>[CH2:26]([O:1][C:2]1[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([F:13])([F:15])[F:14])=[C:7]([N+:21]([O-:24])=[O:22])[CH:6]=2)[CH3:27]

Participants

8

Reactant 4

HCID 1140TolueneHCID 6340IodoethaneHCID 24434Potassium NitrateHCID 387928HCID 387928, compound

Product 1

HCID 18369162HCID 18369162, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 1118Sulfuric AcidSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of ethyl 3,4-dihydro-3-oxo-6-trifluoromethylquinoxaline-2-carboxylate (500 mg, 1.75 mmol) in concentrated sulfuric acid (5 ml) was added potassium nitrate (354 mg, 3.50 mmol) at 40° C., and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was poured into ice water (100 ml), which was extracted with ethyl acetate. After dried over anhydrous sodium sulfate, solvent was distilled off. Silver oxide (I)(811 mg, 3.50 mmol) was added to the residue obtained which was suspended into toluene (10 ml). Then, iodoethane (280 μl, 3.50 mmol) was added dropwise at 100° C. and the mixture was refluxed for 2 hours. After cooling, the insolubles were filtered off using celite and the solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [hexane-ethyl acetate=8:1] to obtain 255 mg of the title compound as yellowish brown oily product. Yield 41%.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialAfter dried over anhydrous sodium sulfate, solvent
  3. distillationwas distilled off
  4. customobtained which
  5. temperaturethe mixture was refluxed for 2 hours
  6. temperatureAfter cooling
  7. filtrationthe insolubles were filtered off
  8. distillationthe solvent was distilled off
  9. customThe residue obtained

Sources & evidence

ORD record
ord-394f1e170aba4861b7e4218678eeb83c
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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