Diethyl Oxalate → Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

HRID 1693352

Reaktionsgleichung

Reaktionsgleichung von HRID 1693352
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])[CH3:14]

Komponenten

6

Edukt 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 23670592Potassium ethoxide

Produkt 1

HCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of potassium ethoxide (3.1 g, 36.2 mmol) in diethyl ether (70 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (4.9 mL, 36.2 mmol) and the reaction stirred at rt for 30 min. A solution of 4-methyl-3-nitropyridine (5.0 g, 36.2 mmol) in diethyl ether (20 mL) was added resulting in the immediate formation of a dark red precipitate. The reaction mixture was stirred at rt for 72 h, then cooled to 0° C. and filtered. The solid was dissolved in water (500 mL) acidified to pH 4 with acetic acid and the precipitate collected and dried to give the title compound as a red solid. δH (d6 DMSO): 1.27 (3H, t), 4.25 (2H, q), 6.74 (1H, s), 8.34 (1H, d), 8.43 (1H, d), 8.98 (1H, s); m/z (ES+)=239 [M+H]+.

Aufarbeitung

  1. customresulting in the immediate formation of a dark red precipitate
  2. stirringThe reaction mixture was stirred at rt for 72 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in water (500 mL)
  6. customthe precipitate collected
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-478fe2ca9e2e42b381fc2503cdd81988
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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