Sodium Bicarbonate → HCID 15451894, compound

HRID 1637003Notes

Reaction equation

HRID 1637003 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:16][OH:17])[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+]>Cl.O1CCOCC1>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[N:16]\[OH:17])/[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 73604849HCID 73604849, compound

Product 1

HCID 15451894HCID 15451894, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of 2-(2-acetoxymethylphenyl)-2-hydroxyiminoacetamide (388 mg, E/Z=35/65) was dissolved in a 5N hydrogen chloride/dioxane solution (3.3 ml), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate three times. The combined ethyl acetate layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (300 mg). This crude product was crystallized from ethyl acetate-hexane, and the crystallization mother liquor was concentrated under reduced pressure and purified by silica gel thin layer chromatography (ethyl acetate:hexane=4:1) to obtain the title compound (243 mg in total, yield: 62.8%, pale yellow crystals).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined ethyl acetate layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent under reduced pressure
  5. customgave the crude product (300 mg)
  6. customThis crude product was crystallized from ethyl acetate-hexane
  7. concentrationthe crystallization mother liquor was concentrated under reduced pressure
  8. custompurified by silica gel thin layer chromatography (ethyl acetate:hexane=4:1)

Sources & evidence

ORD record
ord-7bcad7f7ae874f2eba70fd7d70db681c
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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