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

HRID 1638834Notes

Reaction equation

HRID 1638834 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-oneYield 62.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (36.42 g) was 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) was dropwise added, and the resultant mixture was heated at 60° to 80° C. under reflux for 3 hours. After removal of residue by filtration, the filtrate was extracted with ethyl acetate. The extract was washed with water and sodium bicarbonate solution, dried and concentrated to give 7-fluoro-2H-1,4-benzoxazin-3(4H)-one (6.82 g). m.p., 186.7° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter removal of residue
  3. filtrationby filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe extract was washed with water and sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-989b82dca4bd4afa8790b83f86c7b710
Source dataset
uspto-grants-1989_11
Patent number
US04880925

Reaction notes

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