p-Toluenesulfonic acid → 3-[1,3-Dioxo-4-benzamidoisoindolin-2-yl]-2,6-dioxo-5-hydroxypiperidine

HRID 989792Notes

Reaction equation

HRID 989792 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:20])[N:3]1[CH:21]1[CH2:26][CH:25]([O:27]C(=O)C)[C:24](=[O:31])[NH:23][C:22]1=[O:32].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([NH:11][C:12](=[O:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:20])[N:3]1[CH:21]1[CH2:26][CH:25]([OH:27])[C:24](=[O:31])[NH:23][C:22]1=[O:32]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22241179HCID 22241179, compound

Product 1

HCID 116826303-[1,3-Dioxo-4-benzamidoisoindolin-2-yl]-2,6-dioxo-5-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[1,3-dioxo-4-benzamidoisoindolin-2-yl]-2,6-dioxo-5-acetoxypiperidine (1.36 g, 3.5 mmol) and p-toluenesulfonic acid (0.33 g, 1.8 mmol) in methanol (20 mL) is heated at reflux for 5 hours. The solvent is removed in vacuo to give 3-[1,3-dioxo-4-benzamidoisoindolin-2-yl]-2,6-dioxo-5-hydroxypiperidine 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-92ef409f17694fbb8a1897eccdd03bb3
Source dataset
uspto-grants-2002_10
Patent number
US06458810B1

Reaction notes

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