Ethanol → HCID 18317742, compound

HRID 1700686Notes

Reaction equation

HRID 1700686 reaction equation
ClC1C=CC=CC=1C1C[C:12](=O)[C:11](=[C:15](O)[CH3:16])C(=O)C1.[ClH:19].N(N=[C:25]1[CH2:33][CH:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:31][C:30]2[NH:29][CH:28]=[C:27]([CH3:40])[C:26]1=2)C(N)=N.[CH2:41]([N:43](CC)CC)[CH3:42].C([OH:50])C>>[CH2:28]([N:29]1[C:30]2[CH2:31][CH:32]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[Cl:19])[CH2:33][C:25](=[O:50])[C:26]=2[C:41]([CH3:42])=[N:43]1)[C:27]1[CH:40]=[CH:12][CH:11]=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 178430811HCID 178430811, compoundHCID 178467253HCID 178467253, compound

Product 1

HCID 18317742HCID 18317742, compound

Procedure

To a solution of 5-(2-chlorophenyl)-2-(1-hydroxyethylidene)cyclohexane-1,3-dione (0.5 g) and benzylhydrazine 2 hydrochloride (0.39 g) in ethanol (30 ml) was added triethylamine (0.42 g), and the mixture was refluxed for 2.5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (ethyl acetate-hexane). The resulting crystals were recrystallized from ethyl acetate-hexane to give 1-benzyl-6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.37 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate-hexane)
  8. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-60d4f62dd6514c8eb263f1ed4c0a5848
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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