Oxalic acid dihydrate → 2,3-Quinoxalinedione, 1,4-dihydro-5,7-bis(trifluoromethyl)-
Reaction equation
N[C:2]1([CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]1[NH2:17])[NH2:3].O.O.[C:20](O)(=[O:24])[C:21](O)=[O:22]>Cl>[F:14][C:13]([F:16])([F:15])[C:5]1[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=[C:2]2[C:4]=1[NH:17][C:20](=[O:24])[C:21](=[O:22])[NH:3]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1,2-diamino-3,5-bis(trifluoromethyl)aniline (94 mg, 0.38 mmol) and oxalic acid dihydrate (53 mg, 0.42 mmol, used as received) in 4N HCl (2 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. under reduced pressure for 2 h, affording 45 mg of crude 5,7-bis(trifluoromethyl)-1,4-dihydro-2,3-quinoxalinedione (40% ) as a yellow powder. The crude compound was dissolved in 1N NaOH (6 mL) and filtered. The filtrate was acidified to pH=5, affording 23 mg of pure 5,7-bis(trifluoromethyl)-1,4-dihydro-2,3-quinoxalinedione. Mp: 305°-8° C. (dec. from 295° C.). IR (KBr, cm-1) 3421, 3235, 1749, 1690, 1631. 1H NMR (DMSO-d6): δ 7.654 (s, 1H); 7.687 (s, 1H); 11.584 (s, 1H); 12.311 (s, 1H). HRMS: calcd for C10F6H4N2O2 (M+) m/z: 298.0176; found: 298.0170.
Workup
- temperaturewas refluxed at 120°-5° C. for 3 h
- customthe liquid layer was removed
- washThe yellow solid was washed by cold water (2×2 mL)
- filtrationcollected by filtration
- customdried at 60° C. under reduced pressure for 2 h
Sources & evidence
- ORD record
- ord-dca6d2d5661349a7962d294c80e31677
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05620979
Reaction notes
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