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

HRID 2078555Notes

Reaction equation

HRID 2078555 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-7da8c00c06d4408389b163ec529f3a80
Source dataset
uspto-grants-2011_04
Patent number
US07928239B2

Reaction notes

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