4-Nitrophthalimide → (5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

HRID 250464

Reaktionsgleichung

Reaktionsgleichung von HRID 250464
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][C:13]2=[O:20])([O-:9])=[O:8].[CH2:21]([O:23][C:24](=[O:27])[CH2:25]Br)[CH3:22]>>[CH2:21]([O:23][C:24](=[O:27])[CH2:25][N:14]1[C:13](=[O:20])[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=2)[C:15]1=[O:19])[CH3:22]

Komponenten

4

Edukt 3

HCID 69694-NitrophthalimideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 784823(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl esterAusbeute 611,2 %

Versuchsvorschrift

Potassium carbonate (57.8 g) was added to a solution mixture of 5-nitro-isoindole-1,3-dione (26.2 g) and bromo-acetic acid ethyl ester (25.1 g) in actone (500 ml). The resulting mixture was refluxed overnight (18 h). After cooling, reaction mixture was filtered and rinsed with ethyl acetate. Filtrate was concentrated and the residue was triturated with ether (200 ml). Solid was collected and rinsed with ether. Dried in vacuo to give the title compound 231.9 g. 1H NMR (200 MHz, CDCl3) δ 8.69 (m, 2H), 8.07 (d, J=8.2 Hz, 1H), 4.48 (s, 2H), 4.24 (q, J=7.0 Hz, 2H), 1.30 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed overnight (18 h)
  2. temperatureAfter cooling
  3. customreaction mixture
  4. filtrationwas filtered
  5. washrinsed with ethyl acetate
  6. concentrationFiltrate was concentrated
  7. customthe residue was triturated with ether (200 ml)
  8. customSolid was collected
  9. washrinsed with ether
  10. customDried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1c30918a772144c6888f44cb5fd3da84
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863292B2

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