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

HRID 21117Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[C:7]2[C:3]=1[CH:4]([OH:23])[N:5]([C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:6]2=[O:13].[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH2:30].CCCCCC>[N+](C1C=CC=CC=1)([O-])=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[NH:31][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:30]=2)=[C:7]2[C:3]=1[CH:4]([OH:23])[N:5]([C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:6]2=[O:13]

Participants

Conditions

Temperature: 130 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-dc4c7a52aea24039a6c5d789334be90e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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