Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Sodium Hydroxide | HCID 14798 | — |
| Edukt | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Edukt | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Edukt | 2-(4-Methoxyphenyl)acetamide | HCID 241868 | — |
| Lösungsmittel | Acetic Acid | HCID 176 | — |
| Produkt | HCID 178489902 | HCID 178489902 | — |
Reaktionsschritte
A mixture of 2-(4-methoxyphenyl)acetamide (1.51 g, 9.14 mmol) and N,N-dimethylformamide dimethyl acetal (6 ml, 45.0 mmol) in a r.b.f, equipped with a Dean-Stark trap was placed in a 120° C. bath (turned to solution once heated) for 1.5 hours. The reaction was cooled and concentrated, then, added AcOH (18 ml), hydrazine hydrate (0.611 ml, 10.06 mmol), and heated at 90° C. for 1.5 hours. After cooling to RT, added 2M aqueous sodium hydroxide and extracted 3 times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with MeOH in DCM to afford the title compound. Mass spectrum (ESI) 190.3 (M+1).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09221834B2 |
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| Quelldatensatz | uspto-grants-2015_12 |
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| ORD ID | ord-69a8d72d0a1e46c0a07cfe93eb821612 |
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| Quellennotiz | uspto-grants-2015_12 |
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