Oxalic Acid → HCID 22903568, compound

HRID 1488972Notes

Reaction equation

HRID 1488972 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[CH:10]=[CH:9]2)=[CH:6][C:5]([NH2:15])=[C:4]([NH2:16])[CH:3]=1.[C:17](O)(=[O:21])[C:18](O)=[O:19]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[N:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH:10]=[CH:9]1)[NH:15][C:18](=[O:19])[C:17](=[O:21])[NH:16]2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 22903575HCID 22903575, compound

Product 1

HCID 22903568HCID 22903568, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

First, a mixture containing 1.93 g of 4-chloro-5-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamine, 2.21 g of oxalic acid, and 40 ml of 2N hydrochloric acid was refluxed by heating in an oil bath for 2 hours. The mixture was cooled and precipitated crystals were filtered to give 2.1 g of crude crystals of 6-chloro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione (melting point: >400° C.). Then, 500 mg of the crude crystals were recrystallized with dimethylformaldehyde and water to give 299 mg of 6-chloro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione.

Workup

  1. temperaturewas refluxed
  2. temperatureby heating in an oil bath for 2 hours
  3. temperatureThe mixture was cooled
  4. customprecipitated crystals
  5. filtrationwere filtered
  6. customto give 2.1 g of crude crystals of 6-chloro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione (melting point: >400° C.)
  7. customThen, 500 mg of the crude crystals were recrystallized with dimethylformaldehyde and water

Sources & evidence

ORD record
ord-61abab355aa84938818de829d98334c9
Source dataset
uspto-grants-1997_10
Patent number
US05677305

Reaction notes

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