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

HRID 550894

Reaktionsgleichung

Reaktionsgleichung von HRID 550894
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[CH3:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>C(O)C>[N+:19]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:13]=1[CH2:12][C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8])([O-:21])=[O:20]

Komponenten

5

Edukt 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 5360545Sodium

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 930 mg of sodium in 50 mL of absolute ethanol are rapidly added 26 mL of diethyl oxalate. The reaction medium is stirred for 15 minutes at 20° C. A solution of 3.8 g of 4-methyl-3-nitropyridine in 50 mL of absolute ethanol is then added dropwise over 1 hour. The reaction medium is stirred for 4 hours at a temperature in the region of 20° C. and then concentrated under reduced pressure. The residue is taken up in 100 mL of ethyl ether and then filtered. The solid is stirred with 40 mL of 5N hydrochloric acid and then filtered, washed with water and dried under vacuum at 40° C. to give 6.2 g of ethyl 3-(3-nitro-4-pyridyl)-2-oxopropionate having the following characteristics:

Aufarbeitung

  1. stirringThe reaction medium is stirred for 4 hours at a temperature in the region of 20° C.
  2. concentrationconcentrated under reduced pressure
  3. filtrationfiltered
  4. stirringThe solid is stirred with 40 mL of 5N hydrochloric acid
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-1a64d812e44e4c1fb937939e0611cd98
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947706B2

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