3-Nitrobenzaldehyde → 2-Ethoxyethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

HRID 614590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614590
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])=[O:17])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 814132-Ethoxyethyl acetoacetate

Produkt 1

HCID 545745632-Ethoxyethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 3-nitrobenzaldehyde (4.54 g), 2-ethoxyethyl acetoacetate (5.23 g) and piperidine (85.2 mg) in benzene (15 ml) was refluxed under azeotropic dehydration for 3 hours. The resultant mixture was washed with water, an aqueous solution saturated with sodium chloride and water in turn, dried and concentrated to give an oil of 2-ethoxyethyl 2-(3-nitrobenzylidene)acetoacetate. To this oily product was added ethyl 3-amino-4,4-diethoxycrotonate (6.5 g). The mixture was heated at 110° C. for about 3 hours. The reaction mixture was dissolved in ethyl acetate and washed with water twice and dried. The solvent was removed from the mixture to give an oil (15.58 g). This oil was subjected to column chromatography on silica gel with an eluent (a mixture of 10 parts of benzene and one part of ethyl acetate by volume) to give an oily substance (8.09 g). This oily substance (0.93 g) was treated with a mixture of n-hexane and diethyl ether to give crystals, which were further recrystallized from a mixture of n-hexane and diethyl ether to give yellow granules (565.2 mg) of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 99° to 100° C.

Aufarbeitung

  1. temperaturewas refluxed under azeotropic dehydration for 3 hours
  2. washThe resultant mixture was washed with water
  3. dry with materialan aqueous solution saturated with sodium chloride and water in turn, dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f96603083a19414db3294c10b20d3ec8
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145432

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