Methyl acetoacetate → dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4669

Reaktionsgleichung

Reaktionsgleichung von HRID 4669
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[CH:9]=O.[C:18]([O:24][CH3:25])(=[O:23])[CH2:19][C:20]([CH3:22])=O.[NH2:26]/[C:27](/[CH3:33])=[CH:28]\[C:29]([O:31][CH3:32])=[O:30]>C(O)(C)C>[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[CH:9]1[C:19]([C:18]([O:24][CH3:25])=[O:23])=[C:20]([CH3:22])[NH:26][C:27]([CH3:33])=[C:28]1[C:29]([O:31][CH3:32])=[O:30]

Komponenten

5

Edukt 3

HCID 7757Methyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 140504962-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde

Produkt 1

HCID 14050497dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

5.2 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde, 2.4 g of methyl acetoacetate and 2.3 g of methyl 3-aminocrotonate was dissolved in 30 ml of iso-propanol, and the solution obtained was refluxed for 3.5 hours under heating. After cooling, the precipitated crystals were collected by filtration to give 4.4 g of dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. (mp. 206°-207° C.). The product obtained was used directly for the next process without purification.

Aufarbeitung

  1. customthe solution obtained
  2. temperaturewas refluxed for 3.5 hours
  3. temperatureunder heating
  4. temperatureAfter cooling
  5. filtrationthe precipitated crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-062c826e74c641139e59148b875c82f5
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727082

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