5-Hydroxyisoindoline-1,3-dione → 5-Hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 598442Notes

Reaction equation

HRID 598442 reaction equation
[OH:1][C:2]1[CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1)=O>CC(O)=O.[Zn]>[OH:1][C:2]1[CH:12]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:10](=[O:11])[NH:9][CH2:7]2

Participants

4

Reactant 1

HCID 105589505-Hydroxyisoindoline-1,3-dione

Product 1

HCID 225942075-Hydroxy-2,3-dihydro-1H-isoindol-1-oneYield 20.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-hydroxyphthalimide (19.8 g, 121 mmol) in AcOH (500 mL) was slowly added zinc dust (47.6 g, 729 mmol) in portions, then the mixture was heated at the reflux temp. for 40 min., filtered hot, and concentrated under reduced pressure. The reaction was repeated on the same scale and the combined oily residue was purified by column chromatography (1.1 Kg SiO2; gradient from 60% EtOAc/40% hexane to 25% MeOH/75% EtOAc) to give 5-hydroxyisoindolin-1-one (3.77 g): TLC (100% EtOAc) Rf 0.17; HPLC ES-MS m/z 150 ((M+H)+).

Workup

  1. temperaturethe mixture was heated at the reflux temp
  2. filtrationfiltered hot
  3. concentrationconcentrated under reduced pressure
  4. customthe combined oily residue was purified by column chromatography (1.1 Kg SiO2; gradient from 60% EtOAc/40% hexane to 25% MeOH/75% EtOAc)

Sources & evidence

ORD record
ord-58156cafe1724c14810cf0c6f887d085
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Reaction notes

Loading…