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

HRID 1761021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1761021
[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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d0a10769b8b847289082a14e60c453a1
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06846832B2

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