2-Chlorobenzaldehyde → Phthalimidoamlodipine

HRID 652077

Reaktionsgleichung

Reaktionsgleichung von HRID 652077
[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.[C:18]1(=[O:40])[N:22]([CH2:23][CH2:24][O:25][CH2:26][C:27](=O)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:21](=[O:35])[C:20]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:19]12>C(O)(C)C>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH3:8])[NH:1][C:27]([CH2:26][O:25][CH2:24][CH2:23][N:22]2[C:21](=[O:35])[C:20]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:19]3[C:18]2=[O:40])=[C:28]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Komponenten

5

Edukt 3

HCID 69962-ChlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 9840027Ethyl 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate

Produkt 1

HCID 9871958Phthalimidoamlodipine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Methyl 3-aminocrotonate (72.2 g; 0.627M) and 2-chlorobenzaldehyde (88.1 g; 0.627M) were added to a solution of ethyl 4-(2-phthalimidoethoxy)acetoacetate (200 g; 0.627M) in isopropanol (1 liter) and the mixture was heated under reflux for 20 hours. The isopropanol was evaporated under reduced pressure and replaced by acetic acid (1 liter). After granulation at 10° the solid was collected and slurried in methanol (300 ml). The solid was collected by filtration and dried in vacuo at 50° to afford the title compound, yield 84.4 g, m.p. 146°-147°.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customThe isopropanol was evaporated under reduced pressure
  4. customAfter granulation at 10° the solid was collected
  5. filtrationThe solid was collected by filtration
  6. customdried in vacuo at 50°

Quellen und Nachweise

ORD-Eintrag
ord-a4ce0027ed954f5eafb3d35b6c7d99f5
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670449

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