Hydrochloric Acid → 6-fluoro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione

HRID 1488971Notes

Reaction equation

HRID 1488971 reaction equation
[F: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>>[F: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 3

HCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 229035734-fluoro-5-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamine

Product 1

HCID 229035796-fluoro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dioneYield 73.7%

Procedure

First, 4.266 g of 4-fluoro-5-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamine, and 1.927 g of oxalic acid were added to 48 ml of 4N hydrochloric acid. The mixture was refluxed by heating for 2.5 hours. After the reaction, precipitated crystals were filtered, washed with water, and dried to give 3.920 g of 6-fluoro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureby heating for 2.5 hours
  3. customAfter the reaction
  4. customprecipitated crystals
  5. filtrationwere filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-66e8effa2d1948cdb867e148a3a4f9f6
Source dataset
uspto-grants-1997_10
Patent number
US05677305

Reaction notes

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