Ethyl 2-(5-fluoro-2-nitrophenoxy)acetate → 7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 1030959Notes

Reaction equation

HRID 1030959 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH:14]=1)[O:7][CH2:8][C:9](OCC)=[O:10]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:15][C:9](=[O:10])[CH2:8][O:7][C:6]=2[CH:14]=1

Participants

5

Reactant 1

HCID 13752803Ethyl 2-(5-fluoro-2-nitrophenoxy)acetate

Product 1

HCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (36.42 g) is suspended in 5% aqueous acetic acid (69 ml) and heated to 80° C. To the suspension, a solution of ethyl 5-fluoro-2-nitrophenoxyacetate (15.86 g) in acetic acid (65 ml) and ethyl acetate (65 ml) is dropwise added, and the resulting mixture is heated at 60° to 80° C. under reflux for 3 hours. After removal of residue by filtration, the filtrate is extracted with ethyl acetate. The extract is washed with water and sodium bicarbonate solution, dried and concentrated to give 7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine.

Workup

  1. temperaturethe resulting mixture is heated at 60° to 80° C.
  2. temperatureunder reflux for 3 hours
  3. customAfter removal of residue
  4. filtrationby filtration
  5. extractionthe filtrate is extracted with ethyl acetate
  6. washThe extract is washed with water and sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-47a21b85ac1c4cbebd79e156d12889f4
Source dataset
uspto-grants-1992_04
Patent number
US05108488

Reaction notes

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