Triethylamine → 3-Oxo-1-cyclohexenyl 1-methyl-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 240326Notes

Reaction equation

HRID 240326 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]1=[O:15].C(Cl)(=O)C(Cl)=O.[C:22]1(=O)[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][C:22]2[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH:23]=2)=[O:13])[C:3]1=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 129004164-Methyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylic acid

Product 1

HCID 675324763-Oxo-1-cyclohexenyl 1-methyl-2-oxo-1,2-dihydroquinoxaline-3-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

4.6 g (22.5 mmol) of 1-methyl-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid was dissolved in dichloromethane (200 mL), and N,N-dimethylformamide (0.5 mL) and 4.3 g (33.9 mmol) of oxalyl chloride were added thereto. The mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in dichloromethane (100 mL). This solution was added dropwise at room temperature to a solution prepared by dissolving 2.8 g (25.0 mmol) of 1,3-cyclohexanedione and 2.7 g (26.7 mmol) of triethylamine in dichloromethane (100 mL). The mixture was stirred for 1 hour at room temperature, and then, the reaction mixture was washed with water, and dried over anhydrous sodium sulfate. The inorganic matter was separated by filtration, and then the solvent was distilled off under reduced pressure, to obtain 6.3 g (yield 94%) of 3-oxo-1-cyclohexenyl 1-methyl-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in dichloromethane (100 mL)
  3. additionThis solution was added dropwise at room temperature to a solution
  4. customprepared
  5. stirringThe mixture was stirred for 1 hour at room temperature
  6. washthe reaction mixture was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe inorganic matter was separated by filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-13bc1f72fe374f3d83c07e8f753fafb2
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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