Triethylamine → Ethyl 5-[amino(hydroxyimino)methyl]pyrazine-2-carboxylate

HRID 2242223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242223
C(N(CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[CH:18]=[N:17][C:16]([C:19]#[N:20])=[CH:15][N:14]=1)=[O:12])[CH3:9].Cl.[NH2:22][OH:23]>CCO>[NH2:20][C:19](=[N:22][OH:23])[C:16]1[N:17]=[CH:18][C:13]([C:11]([O:10][CH2:8][CH3:9])=[O:12])=[N:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 686492385-Cyano-pyrazine-2-carboxylic acid ethyl ester

Produkt 1

HCID 136368376Ethyl 5-[amino(hydroxyimino)methyl]pyrazine-2-carboxylateAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Triethylamine (7.08 mL, 51.9 mmol) was added to a solution of 5-cyano-pyrazine-2-carboxylic acid ethyl ester (4.0 g, 22.6 mmol), hydroxylamine hydrochloride (3.45 g, 49.7 mmol) and EtOH (32 mL) and stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo and dissolved in H2O (30 mL). The aqueous solution was extracted with CHCl3 (3×30 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to yield the title compound (2.95 g, 62%) as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in H2O (30 mL)
  4. extractionThe aqueous solution was extracted with CHCl3 (3×30 mL)
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-61fa46744f05455282fc975e651a52b8
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671043B2

Notizen zur Reaktion

Wird geladen…