5-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione → 5-(4-Aminophenoxy)isoindoline-1,3-dione

HRID 491066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491066
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.O.[Fe]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1

Komponenten

5

Edukt 1

HCID 8675015-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 8826275-(4-Aminophenoxy)isoindoline-1,3-dioneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 5-(4-nitrophenoxy)isoindoline-1,3-dione (0.6 g, 2.11 mmol) in conc. AcOH (12 mL) and water (0.1 mL) was stirred under stream of argon while iron powder (0.59 g, 55.9 mmol) was added slowly. This mixture stirred at room temp. for 72 h, then was diluted with water (25 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give 5-(4-aminophenoxy)isoindoline-1,3-dione as a brownish solid (0.4 g, 75%): TLC (50% EtOAc/50% hexane) Rf0.27; 1H NMR (DMSO-d6) δ 5.14 (brs, 2H), 6.62 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 7.03 (d, J=2.1 Hz, 1H), 7.23 (dd, 1H), 7.75 (d, J=8.4 Hz, 1H), 11.02 (s, 1H); HPLC ES-MS m/z 255 ((M+H)+, 100%).

Aufarbeitung

  1. additionwas added slowly
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1ed34b604d804445b16049420218e368
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528255B2

Notizen zur Reaktion

Wird geladen…