Sodium Bicarbonate → HCID 15451892, compound

HRID 1637007Notes

Reaction equation

HRID 1637007 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][O:17][CH3:18])[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]\[O:17][CH3:18])/[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 53837207HCID 53837207, compound

Product 1

HCID 15451892HCID 15451892, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of 2-(2-acetoxymethylphenyl)-2-methoxyiminoacetamide (793 mg, E/Z=56/44) was dissolved in a 6N hydrogen chloride/dioxane solution (6.3 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate twice. 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 (700 mg). This crude product was crystallized from ethyl acetate-hexane. The crystallization mother liquor was concentrated under reduced pressure and purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to obtain the title compound (616 mg in total, yield: 77.6%, pale yellow crystals).

Workup

  1. extractionextracted with ethyl acetate twice
  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 (700 mg)
  6. customThis crude product was crystallized from ethyl acetate-hexane
  7. concentrationThe crystallization mother liquor was concentrated under reduced pressure
  8. custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-161f5f8c765b4467a889e21422bb86f4
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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