Potassium Iodide → 2-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dione

HRID 2060126Notes

Reaction equation

HRID 2060126 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8].[OH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[C:12](=[O:29])[N:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:14]2=[O:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:13]2[C:12](=[O:29])[C:11]3[C:15](=[CH:16][CH:17]=[CH:18][C:10]=3[O:9][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH3:8])[C:14]2=[O:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptane2×HCID 592631454-Hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione

Product 1

HCID 592631332-(4-Methoxy-benzyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-isoindole-1,3-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-Bromo-ethoxy)-2-methoxy-ethane (107 mg, 0.58 mmol) was added to a suspension of 4-hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione (150 mg, 0.53 mmol) and potassium carbonate (200 mg, 1.4 mmol) in DMF (2 mL). After 3.5 hours, a catalytic amount of potassium iodide was added. After a further 17 hours, the mixture was warmed to 60° C. After 3 hours, an additional amount of 1-(2-bromo-ethoxy)-2-methoxy-ethane (20 mg, 0.11 mmol) was added and the mixture maintained at 60° C. for a further 20 hours. The mixture was concentrated in vacuo then the residue was taken up in ethyl acetate and washed with potassium carbonate solution and brine. The organic phase was dried (MgSO4) and concentrated to give the title compound as a yellow oil (149 mg, 73%). 1H NMR (methanol-d4) 7.71 (1H, t), 7.43-7.40 (2H, m), 7.31-7.27 (2H, m), 6.87-6.83 (2H, m), 4.71 (2H, s), 4.37-4.34 (2H, m), 3.92-3.89 (2H, m), 3.77-3.74 (5H, m), 3.55-3.53 (2H, m), 3.33 (3H, s). MS: [M+H]+ 386.

Workup

  1. waitAfter a further 17 hours
  2. waitAfter 3 hours
  3. temperaturethe mixture maintained at 60° C. for a further 20 hours
  4. concentrationThe mixture was concentrated in vacuo
  5. washwashed with potassium carbonate solution and brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d07167a562f4295b2489e27e6ae8e52
Source dataset
uspto-grants-2012_10
Patent number
US08277807B2

Reaction notes

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