Ethyl Acetoacetate → Diethyl 4-[4-(1H-imidazol-1-yl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 2379416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379416
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.[NH4+:23].[OH-:24]>C(O)C>[CH3:18][C:16]1[NH:23][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH2:21][CH3:22])=[O:24])[CH:10]([C:9]2[CH:12]=[CH:13][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:7][CH:8]=2)[C:15]=1[C:14]([O:20][CH2:21][CH3:22])=[O:19]

Komponenten

5

Edukt 3

HCID 8868Ethyl AcetoacetateHCID 14923Ammonium HydroxideHCID 7365304-(1H-imidazol-1-yl)benzaldehyde

Produkt 1

HCID 10475789Diethyl 4-[4-(1H-imidazol-1-yl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 17.2 g (0.1 mol) of 4-(1H-imidazol-1-yl)benzaldehyde, 26 g (0.2 mol) of ethyl acetoacetate and 5 ml of concentrated NH4OH in absolute ethanol (25 ml) was refluxed for 6 hours. The mixture was poured into 500 ml of ice-water and the aqueous solution was extracted with methylene chloride. The organic layers were put together, dried over CaCl2 and evaporated under vacuum. The crude product was recrystallized from Et2O, giving 25.7 g (65%) of 1,4-dihydro-2,6-dimethyl-4-[4-(1H-imidazol-1-yl)phenyl]-3,5-pyridinedicarboxylic acid, diethyl ester, m.p. 231°-233° C.

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. extractionthe aqueous solution was extracted with methylene chloride
  3. dry with materialdried over CaCl2
  4. customevaporated under vacuum
  5. customThe crude product was recrystallized from Et2O

Quellen und Nachweise

ORD-Eintrag
ord-30c38d9714954b91b75fb3cf10a5e076
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05362729

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