Isoindoline → N-(4-methoxy-2-methylphenyl)isoindoline-2-carboxamide

HRID 1453521Notes

Reaction equation

HRID 1453521 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[C:14]([CH3:21])[CH:13]=1>O1CCOCC1>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1]2)=[O:20])=[C:14]([CH3:21])[CH:13]=1

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 27349054-Methoxy-2-methylphenyl isocyanate

Product 1

HCID 57527872N-(4-methoxy-2-methylphenyl)isoindoline-2-carboxamideYield 104.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of isoindoline (576 mg, 4.0 mmol) in dry 1,4-dioxane (20 mL) was added 4-methoxy-2-methylphenyl isocyanate (815 mg, 5.0 mmol) under argon at room temperature. The reaction mixture was then stirred at RT overnight. The solvent was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel (EtOAc/hexanes: 1:1) to give the title compound (1.18 g, 84%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (EtOAc/hexanes: 1:1)

Sources & evidence

ORD record
ord-d7c55b2ee0574a6f8cfad63bc2bd59c1
Source dataset
uspto-grants-2009_01
Patent number
US07476399B2

Reaction notes

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