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

HRID 339418Notes

Reaction equation

HRID 339418 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. 1H NMR (500 MHz, DMSO-d6): δ 2.19 (s, 3H), 3.72 (s, 3H), 4.73 (s, 4H), 6.72 (dd, J=2.5 Hz, 8.5 Hz, 1H), 6.78 (d, J=2.5 Hz, 1H), 7.17 (d, J=8.5 Hz, 1H), 7.30-7.32 (m, 2H), 7.34-7.36 (m, 2H), 7.74 (s, 1H), 13C NMR (DMSO-d6): δ 18.2, 51.9, 55.1, 110.9, 115.1, 122.8, 127.2, 127.8, 130.6, 135.1, 137.0, 154.9, 156.5; MS (MH+, 283); EA calc'd for C17H18N2O2: C, 72.32; H, 6.43; N, 9.92. Found C, 72.16; H, 6.82; N, 9.98.

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-e3c730cfa4814b58af836d213c10d160
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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