7-Fluoroisatoic anhydride → Methyl 2-amino-4-fluorobenzoate

HRID 2371442Notes

Reaction equation

HRID 2371442 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[O:7][C:8](=O)[NH:9][C:4]=2[CH:3]=1.C[O-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5](=[CH:12][CH:13]=1)[C:6]([O:7][CH3:8])=[O:11]

Participants

4

Reactant 2

HCID 100581387-Fluoroisatoic anhydrideHCID 10942334Sodium Methoxide

Product 1

HCID 14075433Methyl 2-amino-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-fluoro-1H-3,1-benzoxazine-2,4-dione (13.5 g) and sodium methoxide (0.2 g) in methanol (30 ml), was heated on a steam bath until vigorous bubbling ceased. It was then heated under reflux for 31/2 hours, cooled, added to aqueous sodium bicarbonate (10%; 300 ml) and extracted with ethyl acetate. The extract was washed with water dried and evaporated to give methyl 4-fluoroanthranilate, mp 68°-70°. (Compound 8).

Workup

  1. temperaturewas heated on a steam bath
  2. customuntil vigorous bubbling
  3. temperatureIt was then heated
  4. temperatureunder reflux for 31/2 hours
  5. temperaturecooled
  6. additionadded to aqueous sodium bicarbonate (10%; 300 ml)
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-f44b21f53983466694b4341ca90b7942
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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