Oxalic Acid → 6-Chloro-5,7-difluoro-1,4-dihydroquinoxaline-2,3-dione

HRID 53799Notes

Reaction equation

HRID 53799 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[C:3]=1[F:11].[C:12](O)(=[O:16])[C:13](O)=[O:14]>Cl>[Cl:1][C:2]1[C:3]([F:11])=[C:4]2[C:5](=[CH:6][C:7]=1[F:8])[NH:9][C:13](=[O:14])[C:12](=[O:16])[NH:10]2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 107024804-Chloro-3,5-difluorobenzene-1,2-diamine

Product 1

HCID 108235056-Chloro-5,7-difluoro-1,4-dihydroquinoxaline-2,3-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 230 mg (1.29 mmol) of 4-chloro-3,5-difluoro-1,2-phenylenediamine and 125 mg (1.38 mmol) of oxalic acid in 4 mL of 2N HCl was refluxed for 3 h and cooled to room temperature. The mixture was filtered and washed by water, dried to leave a brown solid (245 mg, 82%), mp >250° C. 1H NMR (DMSO-d6), 6.921 (d, 1, J=9.61), 12.143 (s, 1), 12.168 (s, 1). MS, 232 (M+, 100), 204 (80), 176 (40), 149 (70), 171 (80). HRMS calcd for C8H335ClF2N2O2, 231.9848, found 231.9851.

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationThe mixture was filtered
  3. washwashed by water
  4. customdried

Sources & evidence

ORD record
ord-b8e5cef2a716411b8bfd122bb555e132
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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