Butanedione → HCID 21846952, compound

HRID 619746Notes

Reaction equation

HRID 619746 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([C:14]3[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=3)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH3:22][C:23](=O)[C:24](=O)[CH3:25]>C(O)C>[CH3:22][C:23]1[C:24]([CH3:25])=[N:21][C:16]2[C:17](=[CH:18][CH:19]=[C:14]([S:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)(=[O:13])=[O:12])[CH:15]=2)[N:20]=1

Participants

4

Reactant 2

HCID 650ButanedioneHCID 21846942HCID 21846942, compound

Product 1

HCID 21846952HCID 21846952, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-(5-isoquinolylsulfonyl)benzenediamine 500 mg (1.7 mmol) and ethanol 10 ml, 2,3-butanedione 1.2 ml was added, and the mixture was heated with stirring for 2 hours at 90° C. The reaction mixture was concentrated under reduced pressure, and ether was added to the resulting residue to crystallize. The crystals were filtered, and 2,3-dimethyl-6-(5-isoquinolylsulfonyl)quinoxaline 490 mg (84.7%) was obtained.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and ether
  4. additionwas added to the resulting residue
  5. customto crystallize
  6. filtrationThe crystals were filtered

Sources & evidence

ORD record
ord-89e0917a46fe485392c44af39925cc61
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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