Acetic Acid → HCID 178516721, compound

HRID 1019866Notes

Reaction equation

HRID 1019866 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.[OH-].[Na+].OO.C(O)(=O)C>CO.ClCCl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([OH:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 229129097-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 178516721HCID 178516721, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one (4.00 g, 24.1 mmol, 1.0 eq), sodium hydroxide (1.93 g, 48.2 mmol, 2.0 eq) and of 3% hydrogen peroxide solution (50 mL) is refluxed for 2 hours, then it is acidified by slow addition of acetic acid. The resulting mixture is cooled to room temperature, the precipitated solid is collected by filtration, washed with ice-water, and dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 7-fluoro-quinoxalin-2-ol as a yellow solid (2.60 g, 69% yield).

Workup

  1. filtrationthe precipitated solid is collected by filtration
  2. washwashed with ice-water
  3. customdried under vacuum
  4. customto give a crude that
  5. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-35435815d12a48838302439f29d9918a
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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