HCID 19990445, compound → 1-Hydroxy-6-(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dione

HRID 346151Notes

Reaction equation

HRID 346151 reaction equation
[C:1]([NH:8][C:9]1[CH:10]=[C:11]([C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=[O:16])([C:3](OCC)=[O:4])=[O:2]>C(O)C.[Pt]>[OH:16][N:15]1[C:14]2[C:9](=[CH:10][C:11]([C:18]([F:21])([F:20])[F:19])=[CH:12][CH:13]=2)[NH:8][C:1](=[O:2])[C:3]1=[O:4]

Participants

4

Reactant 1

HCID 19990445HCID 19990445, compound

Product 1

HCID 199904361-Hydroxy-6-(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dioneYield 36.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-ethoxalylamino-4-nitrobenzotrifluoride (0.61 g, 2 mmol) in 50 ml of 96% ethanol was hydrogenated at atmospheric pressure and room temperature in the presence of 30 mg of 5% platinum on carbon for 5 min. The catalyst was filtered off and washed with ethanol. Acetic acid (10 ml) was added to the filtrate and the solution was refluxed for 1.5 h. The mixture was evaporated to dryness, and the residue was recrystallized from ethanol/water to give 0.18 g (36%) of the title compound. M.p.>220° C. dec.; 1H-NMR (DMSO-d6): 7.40-7.70 (m, 3H, ArH), 12.1 (broad s, 1H, NH); IR (KBr): 1700, 1625 cm-1 ; MS (m/e): 246 (68%, M+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol
  3. additionAcetic acid (10 ml) was added to the filtrate
  4. temperaturethe solution was refluxed for 1.5 h
  5. customThe mixture was evaporated to dryness
  6. customthe residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-0625376e29e642d8aa2aba16dbf870e9
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

Loading…