p-Toluenesulfonic acid → 2-(5-Hydroxy-2,6-dioxopiperid-3-yl)-4-methylisoindoline-1,3-dione

HRID 989784Notes

Reaction equation

HRID 989784 reaction equation
[CH3:1][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>[OH:18][CH:16]1[C:15](=[O:22])[NH:14][C:13](=[O:23])[CH:12]([N:5]2[C:4](=[O:24])[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[CH3:1])[C:6]2=[O:11])[CH2:17]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 120473343-(4-Methyl-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

Product 1

HCID 99438042-(5-Hydroxy-2,6-dioxopiperid-3-yl)-4-methylisoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-methyl-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. The solvent is removed in vacuo to give 2-(5-hydroxy-2,6-dioxopiperid-3-yl)-4-methylisoindoline-1,3-dione. The product can be further purified by column chromatography.

Workup

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

Sources & evidence

ORD record
ord-efae3d6d8a15425dad64df5713b5488e
Source dataset
uspto-grants-2002_10
Patent number
US06458810B1

Reaction notes

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