Acetic acid, [(4-fluoro-2-nitrophenyl)amino]oxo-, ethyl ester → 7-Fluoro-1,4-dihydro-1-hydroxy-2,3-quinoxalinedione

HRID 1974477Notes

Reaction equation

HRID 1974477 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[N+:16]([O-:18])=O)([C:3](OCC)=[O:4])=[O:2]>[Pd].CN(C=O)C>[F:15][C:12]1[CH:11]=[C:10]2[C:9]([NH:8][C:1](=[O:2])[C:3](=[O:4])[N:16]2[OH:18])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 10658712Acetic acid, [(4-fluoro-2-nitrophenyl)amino]oxo-, ethyl ester

Product 1

HCID 106317237-Fluoro-1,4-dihydro-1-hydroxy-2,3-quinoxalinedioneYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5.6 g of 2-ethoxalylamino-5-fluoronitrobenzene and 170 ml of DMF was added 0.3 g of 10% Pd-C, and hydrogenation reaction was carried out at ordinary temperature and pressure. The reaction mixture was then filtered and concentrated under reduced pressure. The resulting residue was recrystallized from ethanol to provide 3.68 g (85%) of 7-fluoro-1-hydroxyquinoxaline-2,3-(1H,4H)-dione

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-068db328e3d749cb93d3bc464b49f557
Source dataset
uspto-grants-1994_02
Patent number
US05283244

Reaction notes

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