Phthalimide → N-Carbethoxyphthalimide

HRID 1483832Notes

Reaction equation

HRID 1483832 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.Cl[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CCN(CC)CC>[O:11]=[C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[N:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 6809PhthalimideHCID 10928Ethyl chloroformate

Product 1

HCID 31187N-CarbethoxyphthalimideYield 56%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of isoindoline-1,3-dione (2 g, 13.6 mmol) in Et3N (60 mL) was added ClCOOEt (2.55 g, 16.33 mmol) at 0° C. The mixture was warmed to room temperature and stirred at room temperature for 4 h. The mixture was filtered and the solid was partitioned between water (150 mL) and EtOAc (50 mL) and adjusted pH value to 6 with 1 N HCl. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated in vacuo to give ethyl 1,3-dioxoisoindoline-2-carboxylate (1.67 g, 53.08%) as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solid was partitioned between water (150 mL) and EtOAc (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-567fc7b9a75e45deacba0b21bf62d19f
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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