p-Toluenesulfonic acid → 4-Nitro-2-(5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1-one

HRID 891989Notes

Reaction equation

HRID 891989 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH:18]([O:20]C(=O)C)[C:17](=[O:24])[NH:16][C:15]1=[O:25])[C:8]2=[O:13])([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH:18]([OH:20])[C:17](=[O:24])[NH:16][C:15]1=[O:25])[C:8]2=[O:13])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 222411953-(4-Nitro-1-oxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

Product 1

HCID 222412004-Nitro-2-(5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-nitro-1-oxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine (0.96 g, 3.5 mmol) and p-toluenesulfonic acid (0.33 g, 1.8 mmol) in methanol (10 mL) is heated at reflux for 5 hours. The solvent is removed in vacuo to give 4-nitro-2-(5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1-one which is further purified by column chromatography.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d3f61b19b1dc4437b32007ccd085d1e3
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

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