Potassium Hydroxide → HCID 178524847, compound

HRID 336353Notes

Reaction equation

HRID 336353 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]([O:16]CC)=[O:15])[C:8]([OH:19])=[N:7]2>CC(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]([OH:16])=[O:15])[C:8]([OH:19])=[N:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178470158HCID 178470158, compound

Product 1

HCID 178524847HCID 178524847, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Potassium hydroxide (1.25 g, 22.2 mmol) was added to a suspension of 6-chloro-2-(ethoxycarbonyl)-3-hydroxyquinoxaline (0.56 g, 2.22 mmol) in 2-propanol (5 mL) and water (7.5 mL) and the resulting solution were heated at reflux for 12 h. The cooled mixture was acidified to pH 2 and the solvents were removed under reduced pressure, after which the residue was taken up in water (50 mL) and extracted with ethyl acetate (2×40 mL). The organic extracts were combined and the solvents were removed under reduced pressure, producing a residue that was purified by flash column chromatography on silica gel, eluting with methanol/methylene chloride (1:9), to provide 6-chloro-3-hydroxyquinoxaline-2-carboxylic acid as a light yellow solid: 1H NMR (400 MHz, CD3OD) δ 7.91 (d, 1H), 7.45 (d, 1H), 7.37 (dd, 1H) ppm; ESI MS m/z 223 [M−H]−.

Workup

  1. temperaturethe resulting solution were heated
  2. temperatureat reflux for 12 h
  3. customthe solvents were removed under reduced pressure
  4. extractionextracted with ethyl acetate (2×40 mL)
  5. customthe solvents were removed under reduced pressure
  6. customproducing a residue that
  7. customwas purified by flash column chromatography on silica gel
  8. washeluting with methanol/methylene chloride (1:9)

Sources & evidence

ORD record
ord-b2df69b9c010420699cf2e5ed89ef0c7
Source dataset
uspto-grants-2014_11
Patent number
US08889683B2

Reaction notes

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