Acetic Acid → 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

HRID 346133Notes

Reaction equation

HRID 346133 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=[O:10])[C:6]([NH:12][C:13]([C:15](OCC)=[O:16])=[O:14])=[CH:5][C:4]=1[C:20]([F:23])([F:22])[F:21])#[N:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([C:3]1[CH:8]=[C:7]2[C:6]([NH:12][C:13](=[O:14])[C:15](=[O:16])[N:9]2[OH:10])=[CH:5][C:4]=1[C:20]([F:23])([F:22])[F:21])#[N:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 199904042-Cyano-5-ethoxalylamino-4-nitrobenzotrifluoride

Product 1

HCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dioneYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 10.5 g (31.7 mmol) 2-cyano-5-ethoxalylamino-4-nitrobenzotrifluoride in 450 ml ethanol was added 45 ml glacial acetic acid. The mixture was hydrogenated at atm. pressure by using 0.2 g 5% Pd-C as a catalyst. The filtered and evaporated reaction product was recrystallized (ethylacetate-light petroleum) to give 6.91 g (81%) of 7-cyano-1-hydroxy-6-trifluoromethyl-quinoxaline-2,3(1H,4H)-dione. M.p. 180° C. decomp. 1H-NMR (DMSO-d6): 7.93 (1H, s), 7.53 (1H, s). MS (m/e): 271 (M+, 70%).

Workup

  1. filtrationThe filtered
  2. customevaporated
  3. customreaction product
  4. customwas recrystallized (ethylacetate-light petroleum)

Sources & evidence

ORD record
ord-012ebff4faa943169b742e1c8e8d8504
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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