Réaction #4765

ord-062c826e74c641139e59148b875c82f5

Équation de réaction

O=Cc1cc([N+](=O)[O-])ccc1OC/C=C/CCl
2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde
COC(=O)CC(C)=O
methyl acetoacetate
COC(=O)/C=C(/C)N
methyl 3-aminocrotonate
COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cc([N+](=O)[O-])ccc1OC/C=C/CCl
dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Rendement 48.8%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe solution obtained
  2. 2
    Températurewas refluxed for 3.5 hours
  3. 3
    Températureunder heating
  4. 4
    TempératureAfter cooling
  5. 5
    Filtrationthe precipitated crystals were collected by filtration

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04727082uspto-grants-1988_02