Water → 2-Benzyl-5-ethylaminoisoindoline

HRID 1494830Notes

Reaction equation

HRID 1494830 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18](=O)[CH3:19])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.O>O1CCCC1>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][CH2:18][CH3:19])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 151678882-Benzyl-5-acetamidoisoindolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 151678892-Benzyl-5-ethylaminoisoindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-benzyl-5-acetamidoisoindoline prepared above was dissolved in 30 ml of anhydrous tetrahydrofuran and to the solution was dropwise added 600 mg of lithium aluminum hydride dissolved in 10 ml of tetrahydrofuran over 10 minutes. After the mixture was refluxed for 2 hours, ether saturated with water was added to it. The resulting precipitatess were removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (chloroform/methanol =25/1) to obtain 2.19 g of 2-benzyl-5-ethylaminoisoindoline as a dark brown oil.

Workup

  1. temperatureAfter the mixture was refluxed for 2 hours
  2. customThe resulting precipitatess were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel (chloroform/methanol =25/1)

Sources & evidence

ORD record
ord-d973dc1d43de4764b7e90536c86cf3f2
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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