Acetic Acid → 3-(4-Amino-2-fluorobenzyl)-1,3-oxazolidin-2-one

HRID 44304Notes

Reaction equation

HRID 44304 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].C(O)(=O)C.[OH-].[Na+]>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[CH:11][C:3]([CH2:4][N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:10])=[C:2]([F:1])[CH:14]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 666368043-(2-Fluoro-4-nitrobenzyl)-1,3-oxazolidin-2-one

Product 1

HCID 647676883-(4-Amino-2-fluorobenzyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound obtained in Step B (10.37 mmoles) in ethanol (25 ml) there are added 122 microliters of acetic acid. The solution is heated at reflux and stirred for 10 minutes. Powdered iron (2.08 g) and 75 mg of FeCl3.6H2O are added. After stirring for 2 hours at reflux, the mixture is brought to ambient temperature and then concentrated to dryness. 50 ml of water are added to the residue obtained, and the pH is made alkaline using sodium hydroxide. The solution is extracted 4 times with AcOEt. The organic phases are combined and washed with saturated aqueous NaCl solution and then dried with MgSO4. After filtration, the organic phase is evaporated to dryness to yield the title product, which is used directly in the next Step.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux
  3. stirringAfter stirring for 2 hours
  4. temperatureat reflux
  5. customis brought to ambient temperature
  6. concentrationconcentrated to dryness
  7. addition50 ml of water are added to the residue
  8. customobtained
  9. extractionThe solution is extracted 4 times with AcOEt
  10. washwashed with saturated aqueous NaCl solution
  11. dry with materialdried with MgSO4
  12. filtrationAfter filtration
  13. customthe organic phase is evaporated to dryness

Sources & evidence

ORD record
ord-cde3bb795efe43af82b7967bb4d995d7
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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