Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Ethyl 5-methoxyindole-2-carboxylate | HCID 20926 | — |
| Edukt | Magnesium | HCID 5462224 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Produkt | HCID 54121458 | HCID 54121458 | 68% |
Reaktionsschritte
To 5-methoxy-1H-indole-2-carboxylic acid ethyl ester (5 g, 22.8 mmol) in MeOH (150 ml) was added magnesium turnings (2.2 g, 91.6 mmol, 4eq.) and the mixture vigorously mechanically stirred (10-30° C.) for 2 hr. 4N HCl was added (to pH1-2), then 25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml). The combined extracts were then washed with satd. NaCl solution (50 ml), dried (Na2SO4) filtered and evaporated. The crude green oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:3) to afford the title compound (3.21g, 15.5 mmol, 68%) as a yellow solid Mp. 59-61° C., MS: m/e=207.1 (M+).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06359138B1 |
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| Quelldatensatz | uspto-grants-2002_03 |
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| ORD ID | ord-86fd5dc6478247c9beb8be490dc96900 |
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| Quellennotiz | uspto-grants-2002_03 |
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