HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 5-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Sodium hydride | HCID 24758 | — |
| Edukt | 2,6-Dimethyl-3-pyridinol | HCID 70732 | — |
| Edukt | 5-Bromo-3-nitropyridine-2-carbonitrile | HCID 2769698 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 5-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile | HCID 67486452 | 101,2% |
Reaktionsschritte
To a 0° C. solution of 2,6-dimethylpyridin-3-ol (10 g, 81.2 mmol) in DMF (50 ml) was added sodium hydride (60% dispersion in oil, 3.4 g, 85 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (18.5 g, 81 mmol) was added and the mixture was allowed to warm slowly to ambient temperature. The reaction mixture was slowly added to 500 mL of rapidly stirring water. A light red solid formed and then the material formed a gum. The gum was extracted into ethyl acetate, and the organics washed with brine, dried over MgSO4 and concentrated in vacuo to afford 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile (25 g, 82 mmol, 101% yield).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08853409B2 |
| Quelldatensatz | uspto-grants-2014_10 |
| ORD ID | ord-d3ebc3b23e2d4d389e88503e7fd5fbc1 |
| Quellennotiz | uspto-grants-2014_10 |