3a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione → Isoindole

HRID 1478008Notes

Reaction equation

HRID 1478008 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1(=O)[NH:11][C:10](=O)[CH:9]2[CH2:13][CH2:14][CH:15]=[CH:16][CH:8]12>C1COCC1>[CH:10]1[NH:11][CH:7]=[C:8]2[C:9]=1[CH:13]=[CH:14][CH:15]=[CH:16]2

Participants

4

Reactant 2

HCID 152779823a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 3013853Isoindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of LAH (22.80 g, 600 mmol) in THF (600 mL) at 0° C. was added tetrahydrophthalimide (39.45 g, 260.9 mmol) portionwise. After addition, the reaction mixture was stirred at 60° C. for 18 h, then cooled down to 0° C. and quenched carefully with water (25 mL) followed by 15% KOH aqueous solution (25 mL) and another 75 mL of water. The resulting mixture was stirred at rt for 1 h, and filtered through a pad of Celite, then washed with DCM (500 mL). The filtrate was concentrated in vacuo to give isoindole as yellow oil, which was used directly in the next reaction.

Workup

  1. additionAfter addition
  2. temperaturecooled down to 0° C.
  3. customquenched carefully with water (25 mL)
  4. stirringThe resulting mixture was stirred at rt for 1 h
  5. filtrationfiltered through a pad of Celite
  6. washwashed with DCM (500 mL)
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7e53cbbaf04447acbde844171999b13d
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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