Ethyl 4-(3-chloropropoxy)benzoate → ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzoate

HRID 346231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346231
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14]Cl)=[CH:7][CH:6]=1)[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[CH:7][CH:6]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoateHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 52199766ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzoateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a stirred solution of 22.5 g (0.092 mole) of 4-(3-chloropropoxy)benzoic acid ethyl ester in 150 mL of dimethylformamide was added 17.6 g (0.093 mole) of potassium phthalimide (98%, Aldrich) and the mixture was heated (135° C.) under a nitrogen atmosphere for 8 hr. The solvent was evaporated under reduced pressure to leave a semi-solid residue. The residue was triturated with 100 mL of water and the resulting solid was collected by filtration. The solid was recrystallized from isopropyl alcohol to yield 18.2 g (55%) of title compound as an off-white solid, mp 106°-108° C.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customto leave a semi-solid residue
  3. customThe residue was triturated with 100 mL of water
  4. filtrationthe resulting solid was collected by filtration
  5. customThe solid was recrystallized from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-5b2a426afd5b47d6ac3fd459e8cc4820
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061720

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