Hydrochloric Acid → HCID 86692813, Verbindung

HRID 518640

Reaktionsgleichung

Reaktionsgleichung von HRID 518640
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][C:6]([OH:12])([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1.Cl>O1CCOCC1.O>[Cl:19][C:20]1[CH:25]=[C:24]([NH:2][CH:3]2[CH2:8][CH2:7][C:6]([OH:12])([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]2)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 122757652,4-Dichloro-5-nitropyridineHCID 66728658HCID 66728658, Verbindung

Produkt 1

HCID 86692813HCID 86692813, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureit was cooled to RT
  2. extractionThe aqueous layer was extracted with DCM (3×40 mL)
  3. dry with materialThe combined organic portions were dried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7cc3e9ec378e44aa90d6429f7fdf8e21
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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