7-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one → 7-fluoroquinoxalin-2(1H)-one

HRID 656987Notes

Reaction equation

HRID 656987 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1>ClCCl.CO.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 229129097-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 217275347-fluoroquinoxalin-2(1H)-oneYield 47.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 7-fluoro-3,4-dihydro-2(1H)-quinoxalinone (15.65 g, 92.88 mmol) in dichloromethane/methanol (1:1, 600 mL) was stirred with manganese dioxide (78.25 g) at room temperature for 1.5 h. The mixture was filtered through kieselguhr, washing through several times with 10% methanol/dichloromethane (˜1 L), and the filtrate was evaporated to give the product (7.27 g). Extraction of the residual filtration solids several times with dimethylformamide at 60-70° C., followed by filtration and evaporation of the extracts, gave more product (6.66 g), the total yield being 13.93 g (91.5%).

Workup

  1. filtrationThe mixture was filtered through kieselguhr
  2. washwashing through several times with 10% methanol/dichloromethane (˜1 L)
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f0ee903346874e259291c5e48da7c0e0
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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