4-Methylbenzylamine → 3-(4-Chlorophenyl)-3-hydroxy-2-(4-methylbenzyl)isoindolin-1-one

HRID 2199305Notes

Reaction equation

HRID 2199305 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2([OH:7])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:12])[N:25]2[CH2:24][C:23]2[CH:26]=[CH:27][C:20]([CH3:19])=[CH:21][CH:22]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 660354-MethylbenzylamineHCID 665642-(4'-Chlorobenzoyl)benzoic acid

Product 1

HCID 513497003-(4-Chlorophenyl)-3-hydroxy-2-(4-methylbenzyl)isoindolin-1-oneYield 74%

Procedure

The named compound was synthesised from 2-(4-chlorobenzoyl)-benzoic acid (2.0 g, 7.6 mmol) and 4-methyl benzylamine (1.07 mL, 8.4 mmol) using General Procedure B, purified by chromatography (Biotage SP4; 10-80% EtOAc/hexane) and obtained as a white solid (2.045 g, 72%).

Workup

  1. custompurified by chromatography (Biotage SP4; 10-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-8325d85daee14550bd8245a0b73a6f8c
Source dataset
uspto-grants-2016_06
Patent number
US09358222B2

Reaction notes

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