4-Nitrophthalic acid anhydride → Ethyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

HRID 10853

Reaktionsgleichung

Reaktionsgleichung von HRID 10853
[NH2:1][CH2:2][CH:3]([C:9]1([CH3:14])[O:13][CH2:12][CH2:11][O:10]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N+:15]([C:18]1[CH:19]=[C:20]2[C:25](=O)[O:24][C:22](=[O:23])[C:21]2=[CH:27][CH:28]=1)([O-:17])=[O:16]>C(Cl)(Cl)Cl>[N+:15]([C:18]1[CH:19]=[C:20]2[C:21](=[CH:27][CH:28]=1)[C:22](=[O:23])[N:1]([CH2:2][CH:3]([C:9]1([CH3:14])[O:10][CH2:11][CH2:12][O:13]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:25]2=[O:24])([O-:17])=[O:16]

Komponenten

4

Edukt 2

HCID 2309764-Nitrophthalic acid anhydrideHCID 21982228Ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Produkt 1

HCID 21982200Ethyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionateAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (800 mg, 3.94 mmol) was dissolved in 15 mL of chloroform, and 4-nitrophthalic anhydride (988 mg, 4.33 mmol) was added to the obtained solution. The resulting mixture was then refluxed at 80° C. for 5 days. After the reaction was completed, the solvent was evaporated by distilling under a reduced pressure. The residue was purified by performing column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain the desired product as a yellow solid (1.24 g, 83%). Rf=0.32 (n-hexane/ethyl acetate=1/1)

Aufarbeitung

  1. customthe solvent was evaporated
  2. distillationby distilling under a reduced pressure
  3. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-803be0e00f494b65b61925570b396a30
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094908B2

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