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

HRID 2255183Notes

Reaction equation

HRID 2255183 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-])=O)=[C:6]([CH:13]=1)[O:7][CH2:8][C:9](OC)=[O:10]>[Pd].CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:14][C:9](=[O:10])[CH2:8][O:7][C:6]=2[CH:13]=1

Participants

4

Reactant 1

HCID 2779697Methyl 2-(5-fluoro-2-nitrophenoxy)acetate

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 500 mg of 5% Pd/C in a Parr bottle was added 100 ml of EtOH followed by 5.0 g (21.8 mmol) of methyl 5-fluoro-2-nitrophenoxyacetate. The flask was placed in a Parr Apparatus, evacuated and then charged with hydrogen. The suspension was then shaken for 2 hours. After evacuating the flask and recharging with nitrogen, the solids were removed by vacuum filtration through Celite®. Since some product does precipitate, the filter cake is repeatedly rinsed with EtOAc (200 ml). The filtrate is refluxed for 4 hours and then evaporated to dryness in vacuo to give the desired material, 7-fluoro-2H-1,4-benzoxazin-3(4H)-one, as a white solid (m.p. 201°-202° C.) in quantitative yield.

Workup

  1. customevacuated
  2. additioncharged with hydrogen
  3. customAfter evacuating the flask
  4. customthe solids were removed by vacuum filtration through Celite®
  5. washthe filter cake is repeatedly rinsed with EtOAc (200 ml)
  6. temperatureThe filtrate is refluxed for 4 hours
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-29edd6f56f2843988f03f783ba47ae6b
Source dataset
uspto-grants-1993_08
Patent number
US05238908

Reaction notes

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