Glyoxal → HCID 21846945, compound

HRID 619745Notes

Reaction equation

HRID 619745 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.[CH:22]([CH:24]=O)=O.S(=O)(O)[O-].[Na+].[OH-].[Na+]>O>[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([C:14]3[CH:15]=[C:16]4[C:17](=[CH:18][CH:19]=3)[N:20]=[CH:24][CH:22]=[N:21]4)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 7860GlyoxalHCID 14798Sodium HydroxideHCID 21846942HCID 21846942, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 21846945HCID 21846945, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-(5-Isoquinolylsulfonyl)-1,2-benzenediamine 300 mg (1.0 mmol) in water, a 40% glyoxal solution 450 mg (3.1 mmol) and sodium bisulfite 650 mg (3.1 mmol) and water 8 ml were added, and the mixture was heated with stirring for 2 hours at 80° C. The reaction mixture was alkalized with 1N sodium hydroxide, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:acetone=5:1), and 6-(5-isoquinolylsulfonyl)quinoxaline 210 mg (66.3%) was obtained.

Workup

  1. temperaturethe mixture was heated
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:acetone=5:1)

Sources & evidence

ORD record
ord-340f8ecc23634d419b880cd182ec5f95
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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