Acetic Acid → HCID 178467258, compound

HRID 1700708Notes

Reaction equation

HRID 1700708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[CH2:10]1.[C:17](O)(=[O:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:10][C:11](=[O:16])[C:12](=[C:17]([OH:19])[CH3:18])[C:13](=[O:15])[CH2:14]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 18317327HCID 18317327, compound

Product 1

HCID 178467258HCID 178467258, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2,5-dichlorophenyl)cyclohexane-1,3-dione (1.5 g), 4-dimethylaminopyridine (1.1 g) and acetic acid (0.63 g) in dimethylformamide (60 ml) was added dicyclohexylcarbodiimide (1.3 g), and the mixture was stirred at room temperature for 36 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was extracted with 1N sodium hydroxide solution, and the aqueous layer was filtered. Insoluble materials were filtered off, and the filtrate was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(2,5-dichlorophenyl)-2-(1-hydroxyethylidene)cyclohexane-1,3-dione (1.4 g), which was dissolved in ethanol (30 ml). To the solution was added hydrazine hydrate (0.26 g), and the mixture was refluxed for 30 minutes. 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, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate-hexane) to give 6-(2,5-dichlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (1.2 g) as colorless crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionThe solution was extracted with 1N sodium hydroxide solution
  4. filtrationthe aqueous layer was filtered
  5. filtrationInsoluble materials were filtered off
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-c4390687a3b64425bf72799a3cad35e0
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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