Butanoic acid, 4-chloro-4-oxo-, ethyl ester → Ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate

HRID 30689

Reaktionsgleichung

Reaktionsgleichung von HRID 30689
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].Cl[C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Komponenten

5

Edukt 3

HCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 516892Sodium BicarbonateHCID 112524674-Nitrobenzylamine hydrochloride

Produkt 1

HCID 47312066Ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-nitrobenzylamine hydrochloride (8.0 g), ethyl 4-chloro-4-oxobutanoate (10.47 g), saturated aqueous sodium hydrogen carbonate (100 ml) and ethyl acetate (100 ml) was stirred at room temperature for 2 hrs. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate (10.3 g, 87%) as colorless prism crystals. melting point: 104-106° C.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-43ba75e21b7741b1b86881fd744ec663
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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