4-Nitrophthalimide → (5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

HRID 409292

Reaction equation

HRID 409292 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:10]1[C:11](=[O:12])[C:6]2[C:7](=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:8]1=[O:9])[CH3:21]

Participants

5

Reactant 3

HCID 69694-NitrophthalimideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 784823(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl esterYield 89.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-nitrophthalimide (82.54 g, 0.43 mol), ethyl bromoacetate (78.92 g, 0.47 mol) and potassium carbonate (130.6 g, 0.94 mol), and acetone (1.5 l) was refluxed for eighteen hours before it was cooled to room temperature, filtered and concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (107.39 g): MS: (+) m/z 279.25 (M+1).

Workup

  1. temperaturewas refluxed for eighteen hours before it
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between dichloromethane and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bff02a827b248418e5164c7a19d1b7f
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Linked notes

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