Phenylhydrazine → HCID 66777263, compound

HRID 2090850Notes

Reaction equation

HRID 2090850 reaction equation
O=[C:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17]OC(OC)N(C)C.[C:25]1([NH:31][NH2:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[C:25]1([N:31]2[CH:17]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 61162Ethyl 3-oxo-5-phenylpentanoateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 66777263HCID 66777263, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-oxo-5-phenylpentanoate (5.8 g) and dimethylformamide dimethylacetal (3.6 mL) was stirred at 100° C. overnight, and the mixture was allowed to cool to room temperature. To the reaction mixture were added ethanol (30 mL) and phenylhydrazine (2.9 g), and the mixture was further stirred at 100° C. for 8 hr. After allowing to cool, ethanol was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio) to give the title object compound (7.1 g, 84%) as a yellow oil.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture was further stirred at 100° C. for 8 hr
  3. temperatureto cool
  4. customethanol was evaporated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio)

Sources & evidence

ORD record
ord-80f9d97bf55249ad856d489c50721e81
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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