p-Toluenesulfonic acid → 1H-Isoindole-1,3(2H)-dione, 4-amino-2-(5-hydroxy-2,6-dioxo-3-piperidinyl)-

HRID 989787Notes

Reaction equation

HRID 989787 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[N:5]([CH:12]1[CH2:17][CH:16]([O:18]C(=O)C)[C:15](=[O:22])[NH:14][C:13]1=[O:23])[C:6]2=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[N:5]([CH:12]1[CH2:17][CH:16]([OH:18])[C:15](=[O:22])[NH:14][C:13]1=[O:23])[C:6]2=[O:11]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 222411893-(4-Amino-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

Product 1

HCID 99220181H-Isoindole-1,3(2H)-dione, 4-amino-2-(5-hydroxy-2,6-dioxo-3-piperidinyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-amino-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine (1 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 and the solvent is then removed in vacuo to give 4-amino-2-(5-hydroxy-2,6-dioxopiperid-3-yl)isoindoline-1,3-dione which can be further purified by column chromatography.

Workup

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

Sources & evidence

ORD record
ord-953c788ecf0a445b96dd7ed1aa13ce04
Source dataset
uspto-grants-2002_10
Patent number
US06458810B1

Reaction notes

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