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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 21117Generated: October 27, 2026

O-Phenylenediamine → 4-chloro-3-hydroxy-7-(1H-benzoimidazol-2-yl)-2-(1-methyl-1-phenylethyl)isoindolinone

https://huagongshe.com/reaction/21117

Reaction equation

Participants

RoleNameHCIDCharge
ReactantO-PhenylenediamineHCID 7243—
ReactantHexaneHCID 8058—
Reactant4-Chloro-3-hydroxy-7-formyl-2-(1-methyl-1-phenylethyl)isoindolinoneHCID 86628232—
SolventNitrobenzeneHCID 7416—
Product4-chloro-3-hydroxy-7-(1H-benzoimidazol-2-yl)-2-(1-methyl-1-phenylethyl)isoindolinoneHCID 6849173934%

Reaction Conditions

Temperature130 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07745641B2
Source datasetuspto-grants-2010_06
ORD IDord-dc4c7a52aea24039a6c5d789334be90e
Source noteuspto-grants-2010_06