Identification | Back Directory | [Name]
6-CYANOOXINDOLE | [CAS]
199327-63-4 | [Synonyms]
6-CYANOOXINDOLE 6-Cyano-2-oxoindole 6-Cyanoindole-2-one 2-Oxindole-6-carbonitrile 2-oxoindoline-6-carbonitrile REF DUPL: 6-Cyano-2-oxoindole 2-Oxo-2H-indole-6-carbonitrile 2-oxo-1,3-dihydroindole-6-carbonitrile 6-Cyano-2-oxindole in stock Factory 2-Oxo-2,3-dihydro-1H-indole-6-carbonitrile 1H-Indole-6-carbonitrile, 2,3-dihydro-2-oxo- 2-oxo-2,3,3a,7a-tetrahydro-1H-indole-6-carbonitrile 2,3-Dihydro-2-oxo-1H-indole-6-carbonitrile, 6-Cyano-2-oxindole | [Molecular Formula]
C9H6N2O | [MDL Number]
MFCD02179606 | [MOL File]
199327-63-4.mol | [Molecular Weight]
158.16 |
Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 2-oxo-2H-indole-6-carbonitrile from zinc cyanide and 6-bromo-2-indolone: Commercially available 6-bromo-2-indolone (656 mg), zinc cyanide (288 mg), and tetrakis(triphenylphosphine)palladium(0) (175 mg) were suspended in anhydrous N,N-dimethylformamide (6 mL). The resulting mixture was degassed by three argon pump/exhaust cycles and subsequently transferred to a preheated oil bath (80°C). After stirring the reaction mixture at a constant temperature for 15 h, it was cooled to room temperature, diluted with deionized water (60 mL) and extracted with ethyl acetate (3 x 60 mL). After combining the organic phases, it was washed with deionized water (2 x 60 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel, dichloromethane/methanol gradient elution) to afford the target product 2-oxo-2H-indole-6-carbonitrile (385 mg, 81% yield). Mass spectrometry analysis showed [M+H]+ peak of 159. | [References]
[1] Patent: US2006/173183, 2006, A1. Location in patent: Page/Page column 105 |
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Energy Chemical
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SynAsst Chemical.
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