Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Methyl Acrylate | HCID 7294 | — |
| Edukt | 4-Bromo-1-naphthylamine | HCID 75303 | — |
| Edukt | Tri-o-tolylphosphine | HCID 80271 | — |
| Edukt | Potassium Acetate | HCID 517044 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Katalysator | Tetrabutylammonium chloride hydrate | HCID 16212273 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 22271930 | HCID 22271930 | 58,1% |
Reaktionsschritte
To a mixture of 4-bromo-1-naphthylamine (4.44 g, 20.0 mmol), potassium acetate (6.28 g, 64.0 mmol), tetrabutylammonium chloride hydrate (6.1 g, 22 mmol), palladium(II)acetate (224 mg, 1.0 mmol) and tri-o-tolylphosphine (1.22 g, 4.0 mmol) was added DMF (60 mL) and methyl acrylate (2.3 mL, 25 mmol). The reaction was heated to 100° C. under N2 for 2 hours, poured into water (300 mL) and extracted with diethyl ether (3×50 mL). The combined ether layers were washed with brine (1×50 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The product was purified on silica gel eluting with 30% ethyl acetate/hexanes to provide the titled compound 2.5 g, 55%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06972340B2 |
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| Quelldatensatz | uspto-grants-2005_12 |
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| ORD ID | ord-67cb650aaed443c6be9a79aeee2a1e7e |
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| Quellennotiz | uspto-grants-2005_12 |
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