Potassium Carbonate → 6-(5-Isoquinolylsulfanyl)quinoxaline

HRID 619743

Reaction equation

HRID 619743 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:12]3[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.O.S(=O)(O)[O-].[Na+].[CH:26]([CH:28]=O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:12]3[CH:13]=[C:14]4[C:15](=[CH:16][CH:17]=3)[N:18]=[CH:28][CH:26]=[N:19]4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154356894-(5-Isoquinolylsulfanyl)-1,2-benzenediamineHCID 23685989Glyoxal-sodium bisulfite hydrate

Product 1

HCID 218469576-(5-Isoquinolylsulfanyl)quinoxalineYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

4-(5-Isoquinolylsulfanyl)-1,2-benzenediamine 200 mg (0.7 mmol) was dissolved in water 10 ml, a water solution 6 ml of glyoxal-sodium bisulfite hydrate 580 mg (2.3 mmol) was added, and the mixture was stirred for 1 hour at 80° C. Potassium carbonate was added to the reaction solution to alkalize the solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:acetone=1:10), and 6-(5-isoquinolylsulfanyl)quinoxaline 90 mg (41.2%) was obtained.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform:acetone=1:10)

Sources & evidence

ORD record
ord-921c43ccfe6d4d018719c5f9ab54e792
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Linked notes

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