HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → 3-(1-Nitro-2-naphthylamino)benzonitrile
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 2-Naphthylamine, 1-nitro- | HCID 11823 | — |
| Edukt | 3-Bromobenzonitrile | HCID 23381 | — |
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Edukt | Binap, (A+-)- | HCID 634876 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Produkt | 3-(1-Nitro-2-naphthylamino)benzonitrile | HCID 67994323 | 37,4% |
Reaktionsschritte
A solution of 1-nitro-2-naphthylamine (875 mg, 4.65 mmol), 3-bromobenzonitrile (846 mg, 4.65 mmol), cesium carbonate (3.03 g, 9.30 mmol), tris(dibenzylidene-acetone)dipalladium(0) (213 mg, 0.23 mmol) and (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (217 mg, 0.35 mmol) in tolunene (10 mL) was heated at 110° C. for 16 hours. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, and was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), to give the titled compound (503 mg, yield 37%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08470814B2 |
| Quelldatensatz | uspto-grants-2013_06 |
| ORD ID | ord-7680b22bb13a4d19a7e6e0ac29a640b1 |
| Quellennotiz | uspto-grants-2013_06 |