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

HRID 571277

Reaction equation

HRID 571277 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

HCID 86681685Tert-butyl 2-(4-amino-1,3-dioxoisoindolin-2-yl)acetateYield 54.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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]+).

Workup

  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)

Sources & evidence

ORD record
ord-cd4541de8ab54b75a17f1a28f87de903
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Linked notes

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