Water → 6-Methoxy-2,3-dihydro-1H-isoindol-1-one

HRID 1761021Notes

Reaction equation

HRID 1761021 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8](CC3C=CC(OC)=CC=3)[C:9]2=[O:12])=[CH:5][CH:4]=1.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce].O>C(#N)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 114375476-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-one

Product 1

HCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-oneYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (300 mg, 1.1 mmol) and ammonium ceric nitrate (2.2 g, 4.0 mmol) in acetonitrile:water (12 mL, 2:1) was stirred at RT for 1 h. Then the mixture was poured into water and extracted with ethyl acetate. The combined extracts were then washed with sodium hydrogen carbonate and water. The organic layer was then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1) to afford the title product (75 mg, 43%) as a light yellow solid. MS m/e=164.2 (M).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were then washed with sodium hydrogen carbonate and water
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1)

Sources & evidence

ORD record
ord-d0a10769b8b847289082a14e60c453a1
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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