5-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazole → (3-Methoxyphenyl)[2-amino-5-[2-(4-chloro-phenyl)-1,3-dioxolan-2-yl]phenyl]methanone

HRID 564829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564829
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:14]=[CH:15][C:16]4[C:17]([CH:29]=3)=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[O:19][N:20]=4)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1>C1COCC1.[Pd]>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:18]([C:17]2[CH:29]=[C:13]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[O:12][CH2:11][CH2:10][O:9]3)[CH:14]=[CH:15][C:16]=2[NH2:20])=[O:19])[CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 1

HCID 227143745-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazole

Produkt 1

HCID 22714351(3-Methoxyphenyl)[2-amino-5-[2-(4-chloro-phenyl)-1,3-dioxolan-2-yl]phenyl]methanoneAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Interm. (5-b) (30 g) in THF (250 ml) was hydrogenated with palladium on carbon (3 g) as a catalyst at room temperature for 12 hours under a 2.6 105 Pa pressure in a Parr apparatus. After uptake of H2 (1 equivalent), the catalyst was filtered through celite and the filtrate was evaporated till dryness. The product was used without further purification, yielding 31.2 g (100%) of (3-methoxyphenyl)[2-amino-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl]methanone (interm. 5-c).

Aufarbeitung

  1. filtrationAfter uptake of H2 (1 equivalent), the catalyst was filtered through celite
  2. customthe filtrate was evaporated till dryness
  3. customThe product was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-082b86dbed21400e8480b4a71156ece0
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169096A

Notizen zur Reaktion

Wird geladen…