Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Acetic Acid | HCID 176 | — |
| Edukt | Water | HCID 962 | — |
| Edukt | Benzyl 2-cyano-2-(4-fluoro-5-methyl-2-nitrophenyl)acetate | HCID 58437495 | — |
| Edukt | HCID 178418361 | HCID 178418361 | — |
| Katalysator | HCID 178418390 | HCID 178418390 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Produkt | 6-fluoro-5-methyl-1H-indole | HCID 2774611 | 76,6% |
Reaktionsschritte
To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08466152B2 |
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| Quelldatensatz | uspto-grants-2013_06 |
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| ORD ID | ord-62b7897db0064c56a669822b4ca8f21c |
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| Quellennotiz | uspto-grants-2013_06 |
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