Tert-butyl 2-(4-nitro-1,3-dioxoisoindolin-2-yl)acetate → Tert-butyl 2-(4-amino-1,3-dioxoisoindolin-2-yl)acetate

HRID 571277

Reaktionsgleichung

Reaktionsgleichung von HRID 571277
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:22])[N:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]2=[O:13])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:22])[N:7]([CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[C:8]2=[O:13]

Komponenten

4

Edukt 1

HCID 7563784Tert-butyl 2-(4-nitro-1,3-dioxoisoindolin-2-yl)acetate

Produkt 1

HCID 86681685Tert-butyl 2-(4-amino-1,3-dioxoisoindolin-2-yl)acetateAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 2-(4-nitro-1,3-dioxoisoindolin-2-yl)acetate (1.44 g, 4.70 mmol) and 10% w/w Pd/C (a catalytic amount) in MeOH (150 ml) was hydrogenated in a Parr apparatus at 25 psi for 3 hours. The catalyst was filtered off and the filtrate was evaporated; the residue was purified by a quick flash chromatography on silica gel (Hexane/EtOAc 1/1) to obtain tert-butyl 2-(4-amino-1,3-dioxoisoindolin-2-yl)acetate (712 mg, 2.58 mmol, 54.8% yield, MS/ESI+ 299.0 [MNa]+).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customthe residue was purified by a quick flash chromatography on silica gel (Hexane/EtOAc 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-cd4541de8ab54b75a17f1a28f87de903
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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