Oxalyl chloride → HCID 68473387, compound

HRID 240336Notes

Reaction equation

HRID 240336 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]([OH:20])=[O:19])[C:9]2=[O:21])[CH:5]=[CH:4][CH:3]=1.[C:22](Cl)(=[O:26])[C:23](Cl)=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]([O:20][C:2]3[CH2:3][CH2:4][CH2:23][C:22](=[O:26])[CH:1]=3)=[O:19])[C:9]2=[O:21])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 67532034HCID 67532034, compound

Product 1

HCID 68473387HCID 68473387, compoundYield 185.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

23.3 g of 1-(6-methyl-2-pyridyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid was dissolved in chloroform (100 mL), and 21.0 g of oxalyl chloride was added thereto. The mixture was stirred for one hour at room temperature. The solvent was distilled off under reduced pressure, and the residue was dissolved in 100 mL of chloroform. 10.2 g of 1,3-cyclohexadione and 10.1 g of triethylamine were added, and the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into water, and extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure, to obtain 28.8 g of 3-oxo-1-cyclohexenyl 1-(6-methyl-2-pyridyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in 100 mL of chloroform
  3. addition10.2 g of 1,3-cyclohexadione and 10.1 g of triethylamine were added
  4. stirringthe mixture was stirred for 2 hours at room temperature
  5. additionThe reaction mixture was poured into water
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5ab4d935a0d044348b3fde6ea2ed39e2
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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