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Water → Ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate

HRID 26701
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 26701
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[C:8](OCC)(=O)[C:9]#[CH:10].O.[C:16]([O:19][CH2:20][CH3:21])(=[O:18])[CH3:17].[CH3:22][N:23]([CH3:26])[CH:24]=[O:25]>>[CH3:22][N:23]1[C:26]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:3]2[CH:1]=[C:17]([C:16]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[C:4]2[C:24]1=[O:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 12182Ethyl propiolate

Produkt 1

HCID 14067565Ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylateAusbeute 41 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

800 mg of dry triethylamine and then 1.13 g of ethyl propiolate were added to a suspension of 2.3 g of the product of Step B in 50 ml of dimethylformamide and the mixture was heated to 70° C. and then was allowed to stand at room temperature for 2 days. 300 ml of water and 200 ml of ethyl acetate were added thereto and the mixture was stirred. The mixture was decanted and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The combined organic phases were washed with water, dried and filtered. The filtrate was evaporated to dryness and oil residue was triturated with ether. The mixture was filtered to obtain a 41% yield of ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate which melted at 197°-198° C. after crystallization from ethyl acetate.

Aufarbeitung

  1. customThe mixture was decanted
  2. extractionthe aqueous layer was extracted twice with 50 ml of ethyl acetate
  3. washThe combined organic phases were washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness and oil residue
  7. customwas triturated with ether
  8. filtrationThe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-4afa53559f414ab1b60b358bf660a80d
Quelldatensatz
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04151280

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