Water → HCID 14347811, compound

HRID 2291763Notes

Reaction equation

HRID 2291763 reaction equation
[OH-].[Na+].O.C([O:6][C:7]([CH2:9][N:10]1[C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[O:13][CH2:12][C:11]1=[O:21])=[O:8])C>C(O)C>[C:7]([CH2:9][N:10]1[C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[O:13][CH2:12][C:11]1=[O:21])([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14347814HCID 14347814, compound

Product 1

HCID 14347811HCID 14347811, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (0.7 g) and water (10 ml) were added to a mixture of 4-ethoxycarbonylmethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (3.7 g) and ethanol (20 ml), and the mixture was refluxed under heating for 5 hours. After the reaction, the solvent was concentrated, and dissolved in water (50 ml), and washed with methylisobutyl ketone, the aqueous layer was acidified with hydrochloric acid, and extracted with methyl isobutyl ketone, then dried with anhydrous sodium sulfate. After the solvent was distilled off, the residue was mixed with a mixed solvent of toluene-hexane (1:5), the mixture was filtered off to give the desired 4-carboxymethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (3.2 g). mp. 183°-184° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. customAfter the reaction
  4. concentrationthe solvent was concentrated
  5. dissolutiondissolved in water (50 ml)
  6. washwashed with methylisobutyl ketone
  7. extractionextracted with methyl isobutyl ketone
  8. dry with materialdried with anhydrous sodium sulfate
  9. distillationAfter the solvent was distilled off
  10. additionthe residue was mixed with a mixed solvent of toluene-hexane (1:5)
  11. filtrationthe mixture was filtered off

Sources & evidence

ORD record
ord-f8020db02a6d43b3a240465d28e6676d
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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