Acetic Acid → 2-Chloroethyl 2-[(2-nitrophenyl)methylidene]-3-oxobutanoate

HRID 894657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894657
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][Cl:21])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][Cl:21])=[O:17])([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 108605Butanoic acid, 3-oxo-, 2-chloroethyl ester

Produkt 1

HCID 540729262-Chloroethyl 2-[(2-nitrophenyl)methylidene]-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 2-nitrobenzaldehyde (4.536 g), 2-chloroethyl acetoacetate (4.94 g) and piperidine (110 mg) in benzene (18 ml) and acetic acid (360 mg) was refluxed for an hour under azeotropic dehydration. The reaction mixture was washed with water and dried. The solvent was distilled off to give an reddish oil of 2-chloroethyl 2-(2-nitrobenzylidene)acetoacetate, and thus obtained oil was treated with ethyl 3-amino-4,4-diethoxycrotonate (7.1 g) to give yellow granules of 2-chloroethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 82° to 84° C. (recrystallized from diisopropyl ether).

Aufarbeitung

  1. temperaturewas refluxed for an hour under azeotropic dehydration
  2. washThe reaction mixture was washed with water
  3. customdried
  4. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-66d1d40009064abaa9943e1e585843b2
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284634

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