Water → HCID 19907331, compound

HRID 2371449Notes

Reaction equation

HRID 2371449 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[O:9][C:10](=O)[NH:11][C:6]=2[CH:5]=1.[CH2:16](Br)[CH:17]=C.O>CN(C)C=O>[CH2:10]([NH:11][C:6]1[C:7](=[CH:14][CH:15]=[C:4]([F:3])[CH:5]=1)[C:8]([OH:9])=[O:13])[CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 19907331HCID 19907331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.41 g of 80% suspension in oil) was added to a solution of 7-fluoro-1H-3,1-benzoxazine-2,4-dione (2.5 g) in dimethylformamide (30 ml). The mixture was cooled to keep the temperature below 30° and then stirred for 1 hour until a clear solution was obtained. A solution of allyl bromide (1.2 ml) in dimethylformamide (30 ml) was added dropwise with cooling and the mixture stirred at room temperature overnight. The mixture was poured into water and extracted with dichloromethane. The extract was washed with water, dried and evaporated and the residue added to aqueous sodium carbonate (10%; 20 ml) and stirred for 3 hours, acidified with hydrochloric acid to pH 3, filtered and the solid washed with water and dried to give N-allyl-4-fluoroanthranilic acid, mp 136°-139°. (Compound 21).

Workup

  1. temperatureThe mixture was cooled
  2. customthe temperature below 30°
  3. customwas obtained
  4. temperaturewith cooling
  5. stirringthe mixture stirred at room temperature overnight
  6. extractionextracted with dichloromethane
  7. washThe extract was washed with water
  8. customdried
  9. customevaporated
  10. additionthe residue added to aqueous sodium carbonate (10%; 20 ml)
  11. stirringstirred for 3 hours
  12. filtrationfiltered
  13. washthe solid washed with water
  14. customdried

Sources & evidence

ORD record
ord-00b703bb70f6433393eaab39924312ea
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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