Oxalic acid dihydrate → 7-Chloro-5-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

HRID 439485Notes

Reaction equation

HRID 439485 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].O.O.[C:16](O)(=[O:20])[C:17](O)=[O:18]>Cl.[OH-].[Na+]>[Cl:9][C:5]1[CH:6]=[C:7]2[C:2]([NH:1][C:16](=[O:20])[C:17](=[O:18])[NH:8]2)=[C:3]([C:10]([F:13])([F:11])[F:12])[CH:4]=1

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 27734985-Chloro-3-(trifluoromethyl)benzene-1,2-diamine

Product 1

HCID 106116907-Chloro-5-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedioneYield 50.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,3-diamino-5-chlorobenzotrifluoride (180 mg, 0.86 mmol) and oxalic acid dihydrate (108 mg, 0.86 mmol, used as received) in 2N HCl (4 mL) was refluxed at 120°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed by cold water (2×2 mL), collected by filtration, and dried at 60° C. for 2 h, affording 136 mg of crude title compound (53%) as a yellow powder. The crude title compound was dissolved in 1N NaOH (6 mL) and filtered. The filtrate was acidified to pH=6, affording 115 mg of title compound. Recrystallization from DMSO/H2O gave 95 mg of pure title compound (37%) as yellow microcrystals. Mp: 302°-4° C. (dec. from 295° C.). IR (KBr, cm-1) 3401, 3255, 1754, 1694, 1528. 1H NMR (DMSO-d6): δ7.374 (d, 1H, J=1.8 Hz); 7.474 (d, 1H, J=1.8 Hz); 11.347 (s, 1H); 12.215 (s, 1H). HRMS: calcd for C9H4ClF3N2O2 (M+) m/z: 263.9912; found: 263.9909.

Workup

  1. temperaturewas refluxed at 120°-5° C. for 3 h
  2. customthe liquid layer was removed
  3. washThe yellow solid was washed by cold water (2×2 mL)
  4. filtrationcollected by filtration
  5. customdried at 60° C. for 2 h
  6. customaffording 136 mg of crude title compound (53%) as a yellow powder
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e539c4fdcecb4619bffdf1c493f4ab66
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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