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

HRID 2251827Notes

Reaction equation

HRID 2251827 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[C:17](=[O:18])[NH:16][C:15](=[O:19])[CH:14]([O:20]C(=O)C)[CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:20][CH:14]1[C:15](=[O:19])[NH:16][C:17](=[O:18])[CH:12]([N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10805336HCID 10805336, compound

Product 1

HCID 98786461H-Isoindole-1,3(2H)-dione, 2-(5-hydroxy-2,6-dioxo-3-piperidinyl)-Yield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This example illustrates the preparation of 2-(5-hydroxy-2,dioxo-piperidin-3(2H)-dione) having a molecular weight of about 274.2. A mixture of about 1.0 g (about 3.2 mmol) of acetic acid 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2,6-dioxo-piperdin-3-yl-ester (single diastereomer) prepared according to Teubert, U. et al., Arch. Pharm. Pharm. Med. Chem., 1998, 331, 7 (incorporated herein by reference) and about 0.3 g (about 1.6 mmol) of p-toluenesulfonic acid was refluxed in about 30 ml of methanol for about 5 hours. The solution was allowed to cool to about room temperature. After cooling, the precipitated product was filtered and recrystallized from acetone/petroleum ether (having a boiling point of about 60° to about 80° C.). Alternatively, the precipitated, filtered product was recrystallized from acetonitrile. A yield of about 0.52 g (about a 60% yield) of 2-(5-hydroxy-2,6-dioxo-piperidin-3-yl)-1H-isoindole-1,3[2H]-dione having a melting point of about 195° to about 230° C. resulted.

Workup

  1. customprepared
  2. temperatureto cool to about room temperature
  3. temperatureAfter cooling
  4. filtrationthe precipitated product was filtered
  5. customrecrystallized from acetone/petroleum ether (
  6. filtrationAlternatively, the precipitated, filtered product
  7. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8993b1c97a644d9098628f059343dec8
Source dataset
uspto-grants-2008_01
Patent number
US07320991B2

Reaction notes

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