4-Nitrophthalimide → HCID 41956059, compound

HRID 571310Notes

Reaction equation

HRID 571310 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]2=[O:14])([O-:3])=[O:2].Br[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:7]2=[O:14])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69694-NitrophthalimideHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 41956059HCID 41956059, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-nitroisoindoline-1,3-dione (1.00 g, 5.20 mmol), benzyl 2-bromoacetate (1.225 ml, 7.81 mmol) and K2CO3 (1.079 g, 7.81 mmol) in DMF (10 ml) was heated at 90° C. for 2 hours. The insoluble inorganic salts were filtered off, and the filtrate was diluted with ethyl acetate and washed with 1N HCl and with brine. The organic layer was dried over Na2SO4 and the solvent was removed under vacuum. The residue was purified by crystallization from MeOH to afford benzyl 2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetate (1.39 g, 4.08 mmol, 78% yield, MS/ESI+ not detectable [MH]+).

Workup

  1. filtrationThe insoluble inorganic salts were filtered off
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with 1N HCl and with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed under vacuum
  6. customThe residue was purified by crystallization from MeOH

Sources & evidence

ORD record
ord-f1e2b2f59ca148f1b1bb7cceee355b19
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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