Benzaldehyde → HCID 18317684, compound

HRID 1700683Notes

Reaction equation

HRID 1700683 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=O)[CH2:9]1.Cl.[NH2:17][NH2:18].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][C:10]2[NH:18][N:17]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]=2[C:12](=[O:14])[CH2:13]1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 115031Hydrazinium chlorideHCID 8753605-(2-Chlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 18317684HCID 18317684, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-chlorophenyl)-cyclohexane-1,3-dione (1.0 g), hydrazine hydrochloride (0.31 g) in ethanol (10 ml) was refluxed for 3 hours. To the solution was added benzaldehyde (1.5 g), and the mixture was refluxed for 4 days. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give crystals, which were recrystallized from ethyl acetate-hexane to give 6-(2-chlorophenyl)-3-phenyl-4,5,6,7-tetrahydroindazol-4-one (0.06 g) as crystals.

Workup

  1. temperaturethe mixture was refluxed for 4 days
  2. customUnder reduced pressure, the solvent was evaporated
  3. customthe residue was purified with silica gel column chromatography
  4. customto give crystals, which
  5. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f2e98b90d6384cbbb77a8c82acd22144
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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