Water → HCID 18177290, compound

HRID 337327

Reaction equation

HRID 337327 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11].[C:12]([CH2:15][C:16](=O)[CH3:17])(=O)[CH3:13].O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:16]([CH3:17])=[CH:15][C:12]([CH3:13])=[N:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 31261AcetylacetoneHCID 28494452-Methoxyphenylhydrazine Hydrochloride

Product 1

HCID 18177290HCID 18177290, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.50 g of 2-methoxyphenyl hydrazine hydrochloride was dissolved in 60 ml of ethanol, and 2.06 ml of acetyl acetone was added and heated at reflux for 1 hour. To the reaction mixture was added 150 ml of water, neutralized with saturated aqueous solution of sodium carbonate, and extracted with 150 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to yield 3.88 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. extractionextracted with 150 ml of ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e9c81ae884da4740b800e223fd70c379
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Linked notes

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