3-Nitrobenzaldehyde → Nicardipine Impurity 19

HRID 568935

Reaktionsgleichung

Reaktionsgleichung von HRID 568935
[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].CCCCCC>C(O)C.CC(C)=O>[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

7

Edukt 4

HCID 74493-NitrobenzaldehydeHCID 8058HexaneHCID 6971017AcetoacetateHCID 136714102-Cyanoethyl 3-aminocrotonate

Produkt 1

HCID 10429284Nicardipine Impurity 19Ausbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

9.7 g of 2-nitratoethyl acetoacetate, 7.7 g of 2-cyanoethyl 3-aminocrotonate and 7.6 g of 3-nitrobenzaldehyde in 76 ml of ethanol were heated at reflux for 7 hours. The mixture was treated in a manner similar to that of Referential Example 1, and the crystals thus obtained were applied to a silica gel column chromatography [eluent: a mixture of hexane and acetone (5:3)] and recrystallized from isopropyl alcohol to give 14.5 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(2-nitratoethyl) ester.

Aufarbeitung

  1. temperatureat reflux for 7 hours
  2. additionThe mixture was treated in a manner similar to that of Referential Example 1
  3. customthe crystals thus obtained
  4. customrecrystallized from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-0dca125cae514566a3d1d75fe4e31e20
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04730052

Verknüpfte Notizen

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