Dimethylformamide → HCID 10584029, compound

HRID 1974486Notes

Reaction equation

HRID 1974486 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=O)([C:3](OCC)=[O:4])=[O:2].CN(C=O)C.[Cl-].[NH4+].CO.C(Cl)(Cl)Cl>O.[Zn]>[F:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[N:16]([OH:18])[C:3](=[O:4])[C:1](=[O:2])[NH:8]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 10538968HCID 10538968, compoundHCID 21584188Chloroform methanol

Product 1

HCID 10584029HCID 10584029, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 6.2 g of 2-ethoxalylamino-4-fluoronitrobenzene and 124 ml of DMF was added a solution of 5.64 g of ammonium chloride in 40 ml of water. Then, 5.7 g of zinc dust was added in small portions to the above mixture. The reaction mixture was stirred under TLC (5% methanol-chloroform) monitoring and, when the starting material had disappeared, the mixture was filtered using Celite and washed with hot DMF. The mixture was heated at 100° C. for 3 hours, after which it was ice-cooled and the resulting inorganic salt crystals were filtered off. To the organic layer was added methanol and the resulting crystals were recovered by filtration to provide 2.73 g of 6-fluoro-1-hydroxyquinoxaline-2,3-(1H,4H)-dione.

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with hot DMF
  3. temperaturecooled
  4. filtrationthe resulting inorganic salt crystals were filtered off
  5. additionTo the organic layer was added methanol
  6. filtrationthe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-063188e08e1a42b3be012b8d2eb29d0c
Source dataset
uspto-grants-1994_02
Patent number
US05283244

Reaction notes

Loading…