2-(4-Tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one → 7-Amino-2-(4-tert-butyl-phenyl)-3-methyl-2,3-dihydro-isoindol-1-one

HRID 2251864Notes

Reaction equation

HRID 2251864 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19](O)([CH3:20])[C:18]3[C:13](=[C:14]([N+:22]([O-])=O)[CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:22][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12](=[O:25])[N:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=1)[CH:19]2[CH3:20]

Participants

4

Reactant 1

HCID 690317142-(4-Tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Product 1

HCID 690303807-Amino-2-(4-tert-butyl-phenyl)-3-methyl-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of 2-(4-tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one (170 mg, Step F) and Pd/C (10 wt %, 35 mg) in 10 mL of MeOH was placed under H2 and stirred at RT for 19 h. The mixture was filtered through Celite®, condensed, and the titled compound was obtained as a colorless oil after flash column chromatography (5 to 35% of EtOAc in hexanes). MS (ES+): 295.1 (M+H)+. Calc'd for C19H22N2O-294.39.

Workup

  1. filtrationThe mixture was filtered through Celite®, condensed

Sources & evidence

ORD record
ord-473373dff7974c3fa15f7d83fb129b07
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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