Ethyl bromoacetate → HCID 19907333, compound

HRID 2371444Notes

Reaction equation

HRID 2371444 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.BrC[C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[F:3][C:4]1[CH:5]=[C:6]([NH:11][CH2:10][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:7](=[CH:14][CH:15]=1)[C:8]([OH:9])=[O:13]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 19907333HCID 19907333, compound

Procedure

Sodium hydride (80% in oil; 1.2 g) was added slowly to a stirred suspension of 7-fluoro-1H-3,1-benzoxazine-2,4-dione (7 g). Effervescence occurred and a clear solution was produced. Ethyl bromoacetate (4.5 ml) was added and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated and the residue was diluted with water. The solid (9.5 g) was filtered off and washed with water and hexane and dried. This solid (5.4 g) was added to a solution of sodium carbonate (5.3 g) in water (60 ml). After stirring for 6 hours the undissolved solid was filtered off. The filtrate was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The solid was purified by flash chromatography and recrystallised from diisopropyl ether to give 4-fluoro-N-(ethoxycarbonylmethyl)- anthranilic acid, mp. 123°-125°. (Compound 11).

Workup

  1. customa clear solution was produced
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with water
  4. filtrationThe solid (9.5 g) was filtered off
  5. washwashed with water and hexane
  6. customdried
  7. additionThis solid (5.4 g) was added to a solution of sodium carbonate (5.3 g) in water (60 ml)
  8. stirringAfter stirring for 6 hours the undissolved solid
  9. filtrationwas filtered off
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water
  12. customdried
  13. customevaporated
  14. customThe solid was purified by flash chromatography
  15. customrecrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-89a25914fb754179ae82e703dc8ae3cf
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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