Ethyl 2-oxocyclohexylacetate → HCID 19755365, compound

HRID 1588432Notes

Reaction equation

HRID 1588432 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.O=[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CCO>[CH3:2][O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][C:13]1[CH:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][CH2:16][CH2:17][C:18]2=1

Participants

4

Reactant 2

HCID 91229Ethyl 2-oxocyclohexylacetateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 19755365HCID 19755365, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-methoxyphenylhydrazine hydrochloride (50.0 mmol, 8.73 g) and ethyl 2-oxocyclohexaneacetate (50.0 mmol, 9.21 g) in absolute EtOH (25 ml) was heated at 85° C. for 1 h. After cooling to room temperature the mixture was filtered and the solvent was evaporated. Column chromatography (5% EtOAc in toluene) gave crystalline ethyl 6-methoxy-1,2,3,4-tetrahydrocarbazol-1-ylacetate (7.7 g, 53%).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationwas filtered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6038bb83f2994fdf80749b84e6062144
Source dataset
uspto-grants-1993_06
Patent number
US05221678

Reaction notes

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