Water → HCID 15167903, compound

HRID 1494854Notes

Reaction equation

HRID 1494854 reaction equation
[C:1]1([CH3:31])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH2:19][N:20]4C(=O)C5=CC=CC=C5C4=O)[CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O.NN.O>CO>[C:1]1([CH3:31])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH2:19][NH2:20])[CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 15167902HCID 15167902, compound

Product 1

HCID 15167903HCID 15167903, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21.6 g of 2-(p-toluenesulfonyl)-5-phthalimidomethylisoindoline and 5 ml of hydrazine hydrate was dissolved in 300 ml of methanol and the solution was heated under reflux for 2 hours. After reaction mixture was allowed to cool, 50 ml of water was added to it. The mixture was concentrated to a half volume under reduced pressure. To the residue 500 ml of 10% aqueous sodium hydroxide and 1 liter of chloroform were added and the whole mixture was thoroughly shaken. The chloroform layer was separated and washed with 5% aqueous sodium hydroxide and then with water. After removing the solvent by evaporation, the residue was recrystallized from ether to give 15.0 g of 2-(p-toluenesulfonyl)-5-aminomethylisoindoline.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter reaction mixture
  4. temperatureto cool
  5. concentrationThe mixture was concentrated to a half volume under reduced pressure
  6. additionTo the residue 500 ml of 10% aqueous sodium hydroxide and 1 liter of chloroform were added
  7. customThe chloroform layer was separated
  8. washwashed with 5% aqueous sodium hydroxide
  9. customAfter removing the solvent
  10. customby evaporation
  11. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-eb41cd812031450397370237d8bd1257
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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