Acetic Acid → HCID 16063552, compound

HRID 1993929Notes

Reaction equation

HRID 1993929 reaction equation
CCO[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:21](O)(=O)[CH3:22]>>[CH2:21]([N:20]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:4](=[O:5])[N:19]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:22]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 16063552HCID 16063552, compound

Conditions

Temperature
120 °C

Procedure

To a solution of cyclohexanone-2-carboxylic acid ethylester (0.6 g) in acetic acid (1 mL) in a round bottom flask under argon was added phenylhydrazine (0.38 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 ISCO Combiflash chromatography (eluting with EtOAc/heptane) to afford the desired 2-phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one (0.56 g) as a light brown solid. MS (ESI+): 215.4 ([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 ISCO Combiflash chromatography (eluting with EtOAc/heptane)

Sources & evidence

ORD record
ord-e904886cc2164d16900bb6da0a188193
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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