4-Aminophenol → 1-(4-hydroxyphenyl)pyrrolidine-2,5-dione

HRID 622119Notes

Reaction equation

HRID 622119 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH2:3][CH2:2]1.[CH:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=1>CN(C)C=O.O>[OH:15][C:10]1[CH:11]=[CH:12][C:13]([N:14]2[C:1](=[O:7])[CH2:2][CH2:3][C:4]2=[O:6])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4034-AminophenolHCID 7922Succinic anhydride

Product 1

HCID 9464681-(4-hydroxyphenyl)pyrrolidine-2,5-dioneYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
170 °C

Procedure

A solution of succinic anhydride (100 g, 1 mol) in dimethylformamide (50 g) was added slowly to a stirred solution of p-aminophenol (109 g, 1 mol) in dimethylformamide (150 g) at a temperature between 25° and 30° C. After 1.5 h the reaction mixture was transferred to a film evaporator in which dimethylformamide (160 g) was separated off at a pressure of 0.05 bar and a temperature of 130° C. A solution of p-toluenesulphonic acid (2 g) in methanol (18 g) was added to the residue obtained, the temperature was increased to 170° C. and dimethylformamide and water were evaporated at a pressure of 13 mbar. The brown solid material thus obtained was dissolved in dimethylformamide having a temperature of 90° C., water was added to the solution until it became turbid, the turbid solution was allowed to adopt ambient temperature and the crystals obtained were filtered off. The N-(4-hydroxyphenyl)succinimide was obtained in a yield of 94 % and with a purity of more than 99%.

Workup

  1. customAfter 1.5 h the reaction mixture was transferred to a film evaporator in which dimethylformamide (160 g)
  2. customwas separated off at a pressure of 0.05 bar
  3. customa temperature of 130° C
  4. additionA solution of p-toluenesulphonic acid (2 g) in methanol (18 g) was added to the residue
  5. customobtained
  6. customdimethylformamide and water were evaporated at a pressure of 13 mbar
  7. customThe brown solid material thus obtained
  8. additionwas added to the solution until it
  9. customto adopt ambient temperature
  10. customthe crystals obtained
  11. filtrationwere filtered off

Sources & evidence

ORD record
ord-4cd4e55329f64b3dbf549c1b84a0a2b3
Source dataset
uspto-grants-1988_09
Patent number
US04769402

Reaction notes

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