5-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione → 2-methyl-2,3-dihydro-1H-isoindol-5-amine

HRID 9723

Reaction equation

HRID 9723 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[N:8]([CH3:11])[C:6](=O)[C:5]2=[CH:12][CH:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:11][N:8]1[CH2:9][C:4]2[C:5](=[CH:12][CH:13]=[C:2]([NH2:1])[CH:3]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 7269315-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 219881602-methyl-2,3-dihydro-1H-isoindol-5-amineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.643 g 4-Amino-N-methylphthalimide was suspended in 50 ml THF and added to 1.328 g lithium aluminum hydride in 50 ml THF at room temperature. The mixture was refluxed for 3 hrs, then stirred a further 3 days at room temperature. Excess LAH was destroyed by addition of water and the mixture filtered over celite. An aqueous phase was separated and extracted with CH2Cl2. The combined organic phases were dried and evaporated. The residue was stirred with HCl in MeOH and the evaporated to yield 1.6 g of the title compound as the hydrochlorid salt.

Workup

  1. temperatureThe mixture was refluxed for 3 hrs
  2. customExcess LAH was destroyed by addition of water
  3. filtrationthe mixture filtered over celite
  4. customAn aqueous phase was separated
  5. extractionextracted with CH2Cl2
  6. customThe combined organic phases were dried
  7. customevaporated
  8. stirringThe residue was stirred with HCl in MeOH
  9. customthe evaporated

Sources & evidence

ORD record
ord-a2cdac2f4a86442e912f0760f5d995ae
Source dataset
uspto-grants-2006_08
Patent number
US07091345B2

Linked notes

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