Water → N-Aminophthalimide

HRID 1851080Notes

Reaction equation

HRID 1851080 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.O.[NH2:13]N.O>C(O)C>[NH2:13][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 6809PhthalimideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 74645N-AminophthalimideYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phthalimide powder was added to a solution of hydrazine monohydrate (28.9 mL, 462.4 mmol) in ethanol (415 mL). The resulting solution was stirred at room temperature for 2 minutes and then stirred under reflux for 8 minutes. The resulting mixture was added to icy water to precipitate solid. The resulting solid was filtered, collected, washed with a small volume of water, and then dried in vacuum. The target compound was yielded as white solid (29.5 g, 182.1 mmol, 42% yield).

Workup

  1. stirringstirred
  2. temperatureunder reflux for 8 minutes
  3. customto precipitate solid
  4. filtrationThe resulting solid was filtered
  5. customcollected
  6. washwashed with a small volume of water
  7. customdried in vacuum

Sources & evidence

ORD record
ord-f416ea9e7cc4460ebc0e873c05aa3490
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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