Phthalimide → 2-(4-Amino-2-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

HRID 2351561Notes

Reaction equation

HRID 2351561 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[C:6]([OH:21])[CH:5]=1)([O-])=O.C1(=O)NC(=O)C2=CC=CC=C12>CN(C)C=O.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11](=[O:20])[C:12]3=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]3[C:14]2=[O:15])=[C:6]([OH:21])[CH:5]=1

Participants

5

Reactant 2

HCID 6809PhthalimideHCID 4679558STK266267

Product 1

HCID 198464642-(4-Amino-2-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

40 g of Raney-Nickel (washed neutral) were added to 284 g (1 mol) of N-(4-nitro-2-hydroxyphenyl)-phthalimide in 1.75 liters of dimethyl formamide (DMF) and the phthalimide was hydrogenated under a pressure of 15-20 bar at 60° C. The filtrate was precipitated in 3.5 liters of water, suction filtered, washed and dried. Yield: 230 g=90% of theoretical yield.

Workup

  1. customwas hydrogenated under a pressure of 15-20 bar at 60° C
  2. customThe filtrate was precipitated in 3.5 liters of water
  3. filtrationsuction filtered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-1a7e004ecbc748c1990b3f52ade22d76
Source dataset
uspto-grants-1989_10
Patent number
US04873338

Reaction notes

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