Water → 4-Amino-N-propylphthalimide

HRID 1597387Notes

Reaction equation

HRID 1597387 reaction equation
[H-].[Na+].[NH2:3][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.I[CH2:16][CH2:17][CH3:18].O>CN(C=O)C>[NH2:3][C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:16][CH2:17][CH3:18])[C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 729154-Aminophthalimide

Product 1

HCID 159074134-Amino-N-propylphthalimideYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (493 g, 12.3 mmol) in DMF (10 ml) was added a solution of 4-aminophthalimide (2.00 g, 12.3 mmol) in DMF (10 ml) at 0° C. After stirring at room temperature for 1 h, iodopropane (1.20 ml, 12.3 mmol) was added to this mixture at 0° C. and stirred at room temperature for 28 h. The mixture was poured into water and extracted with AcOEt:toluene=2:1 (150 ml×3). The extract was washed with water, brine, dried (Na2SO4), and concentrated to give yellow solid, which was purified by column chromatography (silica gel: 130 g, CH2Cl2 only to CH2Cl2/MeOH=75/1) to give 1.14 g (45%) of yellow solid.

Workup

  1. stirringstirred at room temperature for 28 h
  2. extractionextracted with AcOEt
  3. washThe extract was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give yellow solid, which
  7. customwas purified by column chromatography (silica gel

Sources & evidence

ORD record
ord-d47ec467b4a94f0088bd7b735c3032bf
Source dataset
uspto-grants-2001_09
Patent number
US06294569B2

Reaction notes

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