4-Nitrophthalimide → HCID 22502087, compound

HRID 1633990Notes

Reaction equation

HRID 1633990 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].[CH:15]1([CH2:18]Br)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:15]1([CH2:18][N:10]2[C:11](=[O:12])[C:6]3=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=[C:7]3[C:8]2=[O:9])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 69694-NitrophthalimideHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 22502087HCID 22502087, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Nitrophthalimide (6.15 g, 32.0 mmol) was dissolved in DMF (60 mL). Cyclopropylmethyl bromide (9.3 mL, 96 mmol) and potassium carbonate (8.85 g, 64.0 mmol) were added and the mixture was heated to 100° C. for 4 hours. The mixture was allowed to cool to room temperature, and then partitioned between water (500 mL) and ethyl acetate (400 mL). The organic phase was collected, dried with Na2SO4, filtered and taken to dryness using rotary evaporation. The residue was dried overnight in a vacuum oven to afford 6.49 g (82%) of pure N-cyclopropylmethyl4-nitrophthalimide as a powder.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water (500 mL) and ethyl acetate (400 mL)
  3. customThe organic phase was collected
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporation
  7. customThe residue was dried overnight in a vacuum oven

Sources & evidence

ORD record
ord-8c8a0481d95b47e984057b70576206e8
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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