3-Nitrobenzaldehyde → Nicardipine Impurity 19

HRID 568933

Reaktionsgleichung

Reaktionsgleichung von HRID 568933
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:8]/[C:9](/[CH3:18])=[CH:10]\[C:11]([O:13][CH2:14][CH2:15][C:16]#[N:17])=[O:12].[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20]>C(O)(C)C>[C:16]([CH2:15][CH2:14][O:13][C:11]([C:10]1[CH:25]([C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:2]([C:1]([OH:7])=[O:6])=[C:3]([CH3:5])[NH:8][C:9]=1[CH3:18])=[O:12])#[N:17]

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 6971017AcetoacetateHCID 136714102-Cyanoethyl 3-aminocrotonate

Produkt 1

HCID 10429284Nicardipine Impurity 19Ausbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

10.3 g of 3-nitratopropyl acetoacetate, 7.7 g of 2-cyanoethyl 3-aminocrotonate and 7.6 g of 3-nitrobenzaldehyde in 76 ml of isopropyl alcohol were heated at reflux for 6.5 hours, and cooled on ice. The crystals which precipitated were collected by filtration, dried, applied to a silica gel column chromatography (eluent: dichloromethane) and recrystallized from ethanol to give 16.4 g of 2,6-dimethyl-4-(3-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(3-nitratopropyl) ester.

Aufarbeitung

  1. temperatureat reflux for 6.5 hours
  2. temperaturecooled on ice
  3. customThe crystals which precipitated
  4. filtrationwere collected by filtration
  5. customdried
  6. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-cf05da0d5c2c4a7cb1ab8b92df4a8cd5
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04730052

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