Triethylamine → 1-(1H-indol-3-yl)ethanone oxime
Reaction equation
C(N(CC)CC)C.[C:8]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=O)[CH3:9].Cl.[NH2:21][OH:22]>C(O)C>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:8](=[N:21][OH:22])[CH3:9])=[CH:12]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Triethylamine (3.93 mL) was added to a solution of 3-acetylindole (500 mg) and hydroxylamine hydrochloride (981 mg) in ethanol (20 mL), and the reaction solution was heated to reflux at 90° C. for 14 hours. The reaction solution was allowed to be cooled to room temperature, the solvent was concentrated under reduced pressure, and ethyl acetate and water were added to the resulting residue and the organic layer was partitioned. The resulting organic layer was washed with brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: ethyl acetate) to obtain 0.53 g of the title compound. The physical properties of the compound are as follows.
Workup
- temperaturethe reaction solution was heated
- temperatureto be cooled to room temperature
- concentrationthe solvent was concentrated under reduced pressure, and ethyl acetate and water
- additionwere added to the resulting residue
- customthe organic layer was partitioned
- washThe resulting organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (elution solvent: ethyl acetate)
Sources & evidence
- ORD record
- ord-524dfbc2009547079e5008e22eb5dc93
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687640B2
Reaction notes
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