Hydrochloric Acid → HCID 11054797, compound

HRID 2299718Notes

Reaction equation

HRID 2299718 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[N:11][OH:12])[C:9]#N)[CH:5]=[CH:6][CH:7]=1.[OH-:13].[K+].C[O:16][CH2:17][CH2:18]O.Cl>C(OCC)(=O)C.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4](/[C:8](=[N:11]/[OH:12])/[C:9]([O:16][CH2:17][CH3:18])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 73884359HCID 73884359, compound

Product 1

HCID 11054797HCID 11054797, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2-(3-bromophenyl)-2-(hydroxyimino)acetonitrile (19.0 g), 4N aqueous solution of potassium hydroxide (100 ml) and 2-methoxyethanol (100 ml) was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature, 1N hydrochloric acid was added to make the solution acidic and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in ethanol (200 ml) and concentrated sulfuric acid (catalytic amount) was added. The reaction mixture was heated under reflux for 48 hours, cooled to room temperature, poured into an aqueous saturated solution of sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl Z-2-(3-bromophenyl)-2-(hydroxyimino)acetate (3.31 g, yield 14%) as a pale-brown oil from an ethyl acetate-hexane (1:3, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethanol (200 ml)
  8. additionconcentrated sulfuric acid (catalytic amount) was added
  9. temperatureThe reaction mixture was heated
  10. temperatureunder reflux for 48 hours
  11. temperaturecooled to room temperature
  12. additionpoured into an aqueous saturated solution of sodium bicarbonate
  13. extractionextracted with ethyl acetate
  14. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  15. dry with materialdried (MgSO4)
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-c69fd03a6cec4670aebe40ec51ebe20c
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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