4-Nitrophthalimide → HCID 8820864, compound

HRID 571291Notes

Reaction equation

HRID 571291 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].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C(#N)C.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]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:7]2=[O:14])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 69694-NitrophthalimideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 8820864HCID 8820864, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-nitroisoindoline-1,3-dione (10.5 g, 53.6 mmol) in a mixture of acetonitrile (80 ml) and DMF (20 ml), potassium carbonate (9.99 g, 72.3 mmol) and tert-butyl 2-bromoacetate (10.29 ml, 69.6 mmol) were added, and the reaction was heated to reflux for 3 hours. The insoluble inorganic salts were filtered off, and the filtrate was evaporated to dryness. The residue was diluted with EtOH (60 ml) and precipitation of the desired product was observed. The precipitate was collected by filtration affording tert-butyl 2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetate (15.7 g, 51.3 mmol, 96% yield, MS/ESI+ 328.9 [MNa]+).

Workup

  1. additionwere added
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe insoluble inorganic salts were filtered off
  5. customthe filtrate was evaporated to dryness
  6. additionThe residue was diluted with EtOH (60 ml) and precipitation of the desired product
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-f773140524c94157b68f7d97dd7f813d
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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