Water → HCID 18543597, compound

HRID 649866Notes

Reaction equation

HRID 649866 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])=[CH:4][CH:3]=1.[BH4-].[Li+].O>O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH2:12][OH:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6171382-(4-Aminophenyl)-1H-isoindole-1,3(2H)-dioneHCID 4148881Lithium borohydride

Product 1

HCID 18543597HCID 18543597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-(4-aminophenyl)phthalimide (332 mg) in tetrahydrofuran (4 mL) is added lithium borohydride (1.0 g) and the mixture is stirred for 1 hour at 25° C. The mixture is poured into water and extracted into ethyl acetate. The ethyl acetate solution is dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a white foam, which when triturated with diethyl ether provides the desired product as a white powder.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe ethyl acetate solution is dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a white foam, which when
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-c9a50ff4ac9d416fa2e00142274e16f8
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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