Phenylhydrazine → HCID 63352721, compound

HRID 1993913Notes

Reaction equation

HRID 1993913 reaction equation
CO[C:3](=[O:10])[CH2:4][C:5]([CH:7]1[CH2:9][CH2:8]1)=O.[C:11]1([NH:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C>[CH:7]1([C:5]2[CH2:4][C:3](=[O:10])[N:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:18]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 63352721HCID 63352721, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl-3-cyclopropyl-3-oxopropionate (17 g) in acetic acid (40 mL) in a round bottom flask under argon was added phenylhydrazine (12.93 g). The mixture was immersed into an oil bath and heated to 120° C. overnight. The reaction vessel was then cooled and the acetic acid was evaporated in vacuo and the remaining solid was dissolved in EtOAc and water. The phases were separated and the aqueous phase was extracted with further EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo and azeotroped with toluene (2×). The crude residue was then purified via trituration with a 1:1 mixture of ether/pentane to afford the desired 5-cyclopropyl-2-phenyl-2,4-dihydro-pyrazol-3-one (20.8 g) as a light brown solid. MS (ESI+): 201.3 ([M+H]+).

Workup

  1. customThe mixture was immersed into an oil bath
  2. temperatureThe reaction vessel was then cooled
  3. customthe acetic acid was evaporated in vacuo
  4. dissolutionthe remaining solid was dissolved in EtOAc
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with further EtOAc
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customazeotroped with toluene (2×)
  12. customThe crude residue was then purified via trituration with a 1:1 mixture of ether/pentane

Sources & evidence

ORD record
ord-45ad6e4dfc81479f901c2de632cdc3fd
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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