Water → HCID 14347812, compound

HRID 2291764Notes

Reaction equation

HRID 2291764 reaction equation
[OH-].[Na+].O.C([O:6][C:7]([CH2:9][N:10]1[C:15]2[CH:16]=[C:17]([N+:21]([O-:23])=[O:22])[C:18]([F:20])=[CH:19][C:14]=2[O:13][CH2:12][C:11]1=[O:24])=[O:8])C>O1CCOCC1>[C:7]([CH2:9][N:10]1[C:15]2[CH:16]=[C:17]([N+:21]([O-:23])=[O:22])[C:18]([F:20])=[CH:19][C:14]=2[O:13][CH2:12][C:11]1=[O:24])([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14347813HCID 14347813, compound

Product 1

HCID 14347812HCID 14347812, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide (0.9 g) and water (20 ml) were added to a mixture of 4-ethoxycarbonylmethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (5.96 g) and 1,4-dioxane (50 ml). The mixture was stirred at room temperature for one day. Afterthe solvent was distilled off, the residue was mixed with water (100 ml), then filtered. The filtrate was acidified with hydrochloric acid, and extracted with methyl isobutyl ketone (150 ml). After the extract was washed with water, it was dried with anhydrous sodium sulfate, and then the solvent was distilled off to give the desired 4-carboxymethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (4.8 g). mp. 177°-183° C.

Workup

  1. distillationAfterthe solvent was distilled off
  2. additionthe residue was mixed with water (100 ml)
  3. filtrationfiltered
  4. extractionextracted with methyl isobutyl ketone (150 ml)
  5. washAfter the extract was washed with water, it
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-54c88cbe7fc14221947618c295cc5408
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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