Hydrochloric Acid → 2-(3-Chloropyrazin-2-yl)acetic acid

HRID 1852893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852893
C([O:3][C:4](=[O:18])[CH:5]([C:11]1[C:16]([Cl:17])=[N:15][CH:14]=[CH:13][N:12]=1)C(OCC)=O)C.[OH-].[Na+].Cl.C(OCC)C>C(O)C>[Cl:17][C:16]1[C:11]([CH2:5][C:4]([OH:18])=[O:3])=[N:12][CH:13]=[CH:14][N:15]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 57950234HCID 57950234, Verbindung

Produkt 1

HCID 717485942-(3-Chloropyrazin-2-yl)acetic acidAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-(3-chloro-pyrazin-2-yl)-malonic acid diethyl ester (10.0 g) in ethanol (100 ml) was added 2M sodium hydroxide (100 ml) and the reaction mixture heated to 60° C. for 4 hours. The reaction mixture was cooled to ambient temperature then poured onto water and 1M hydrochloric acid followed by extraction with ethyl acetate (3×). The combined organic layers were dried (magnesium sulfate), filtered and the filtrate concentrated to give the crude title compound as a yellow solid. The solid was slurried with diethylether to give (3-chloro-pyrazin-2-yl)-acetic acid (4.35 g). MH+=173, RT=0.72 min (Method A).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionfollowed by extraction with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give the crude title compound as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-9bd0462877b64b1f866e74d12d4d9e9c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962628B2

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