Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2,4-Dichloro-5-nitropyridine | HCID 12275765 | — |
| Edukt | 4-Amino-1-hydroxycyclohexanecarboxylic acid hydrochloride | HCID 66728658 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | HCID 86692813 | HCID 86692813 | 62% |
Reaktionsschritte
A 100 mL round bottom flask was charged with 4-amino-1-hydroxycyclohexanecarboxylic acid hydrochloride (0.28 g, 1.431 mmol), potassium carbonate (0.435 g, 3.15 mmol) and water (1.908 mL). To the mixture was added 2,4-dichloro-5-nitropyridine (0.276 g, 1.431 mmol) as a solution in dioxane (0.954 mL). After the resulting mixture was stirred at 60° C. for 24 hours, it was cooled to RT and treated with 2N aqueous HCl to bring the pH to about 4-5. The aqueous layer was extracted with DCM (3×40 mL). The combined organic portions were dried over sodium sulfate and concentrated to afford 4-(2-chloro-5-nitropyridin-4-ylamino)-1-hydroxycyclohexanecarboxylic acid as a yellow solid (0.28 g, 62.0% yield). MS m/z=316.2 [M+H]. Calc'd for C12H14ClN3O5: 315.1.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09115127B2 |
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| Quelldatensatz | uspto-grants-2015_08 |
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| ORD ID | ord-7cc3e9ec378e44aa90d6429f7fdf8e21 |
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| Quellennotiz | uspto-grants-2015_08 |
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