Reaktion #49395

ord-dc4c7a52aea24039a6c5d789334be90e

Reaktionsgleichung

CC(C)(c1ccccc1)N1C(=O)c2c(C=O)ccc(Cl)c2C1O
4-Chloro-3-hydroxy-7-formyl-2-(1-methyl-1-phenylethyl)isoindolinone
Nc1ccccc1N
o-phenylenediamine
CCCCCC
hexane
CC(C)(c1ccccc1)N1C(=O)c2c(-c3nc4ccccc4[nH]3)ccc(Cl)c2C1O
4-chloro-3-hydroxy-7-(1H-benzoimidazol-2-yl)-2-(1-methyl-1-phenylethyl)isoindolinone
Ausbeute 34.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
130°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe obtained solid was collected by filtration
  2. 2
    Sonstigepurified by preparative thin-layer chromatography (hexane/ethyl acetate=2/1, 1/1)

Vorschrift

4-Chloro-3-hydroxy-7-formyl-2-(1-methyl-1-phenylethyl)isoindolinone (100 mg, 0.303 mmol) was dissolved in nitrobenzene (2 mL), and the solution was added with o-phenylenediamine (49 mg, 0.45 mmol), followed by stirring at 130° C. for 5.2 hours. The reaction mixture was added with hexane and the obtained solid was collected by filtration and purified by preparative thin-layer chromatography (hexane/ethyl acetate=2/1, 1/1) to obtain 4-chloro-3-hydroxy-7-(1H-benzoimidazol-2-yl)-2-(1-methyl-1-phenylethyl)isoindolinone (42.8 mg, yield 34%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745641B2uspto-grants-2010_06