2-Chlorobenzaldehyde → {[4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid

HRID 462458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462458
C[O:2][C:3]([CH2:5][O:6][CH2:7][C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:4].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.[NH2:25]/[C:26](/[CH3:32])=[CH:27]\[C:28]([O:30][CH3:31])=[O:29]>CO>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]1[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([CH3:32])[NH:25][C:8]([CH2:7][O:6][CH2:5][C:3]([OH:2])=[O:4])=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 69962-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 13457217Ethyl 4-(methoxycarbonylmethoxy)acetoacetate

Produkt 1

HCID 13457220{[4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acidAusbeute 16,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-(methoxycarbonylmethoxy)acetoacetate (200 g), 2-chlorobenzaldehyde (128.8 g) and methyl 3-aminocrotonate (105.4 g) in methanol (600 ml) was heated under reflux for 16 hours and then evaporated. The residue was treated with 10% aqueous sodium hydroxide solution and the mixture heated under reflux for 1.5 hours, allowed to cool to room temperature, washed three times with dichloromethane, acidified with concentrated hydrochloric acid and extracted into dichloromethane. The dichloromethane extracts were washed with water, dried over magnesium sulphate and evaporated. The residue was recrystallised from ethyl acetate to give the title compound (63 g), m.p. 150°-154° C.

Aufarbeitung

  1. temperatureunder reflux for 16 hours
  2. customevaporated
  3. additionThe residue was treated with 10% aqueous sodium hydroxide solution
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 1.5 hours
  6. washwashed three times with dichloromethane
  7. extractionextracted into dichloromethane
  8. washThe dichloromethane extracts were washed with water
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe residue was recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e1449e369550492ab65cb2a15f2fb1c0
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04515799

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