Sodium Hydroxide → 5-Amino-2-cyclopropyl-1H-isoindole-1,3(2H)-dione

HRID 1814713Notes

Reaction equation

HRID 1814713 reaction equation
[CH:1]1([N:4]2[C:8](=[O:9])[C:7]3=[CH:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=[C:6]3[C:5]2=[O:17])[CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[CH:1]1([N:4]2[C:8](=[O:9])[C:7]3=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=[C:6]3[C:5]2=[O:17])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 22501920HCID 22501920, compound

Product 1

HCID 225017585-Amino-2-cyclopropyl-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Cyclopropyl-4-nitrophthalimide (10.0 g, 43.0 mmol) was dissolved in ethanol (200 mL). Tin (II) chloride dihydrate (49.0 g, 215 mmol) was added, and the mixture was heated to reflux overnight. After cooling, the mixture was poured over crushed ice (1.0 L), and pH adjusted to 6.5 using 1 N NaOH. The mixture was passed through a small bed of celite, and the filtrate was subsequently extracted with ethyl acetate (1.2 L). The organic phase was dried using anhydrous MgSO4, and solvent was removed by rotary evaporation in vacuo, to afford crystalline N-cyclopropyl-4-aminophthalimide. Yield: 6.0 g (69%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. additionthe mixture was poured
  5. extractionthe filtrate was subsequently extracted with ethyl acetate (1.2 L)
  6. customThe organic phase was dried
  7. customwas removed by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-6009209ee4fa45d6a9da8efdffb4de7f
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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