Maleic Anhydride → N-(3-hydroxyphenyl)maleimide

HRID 2118772Notes

Reaction equation

HRID 2118772 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>C(O)(=O)C>[OH:8][C:4]1[CH:3]=[C:2]([N:1]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 115683-Aminophenol

Product 1

HCID 5325833N-(3-hydroxyphenyl)maleimideYield 24.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
25 °C

Procedure

A 54.57 gram portion of m-aminophenol (0.50 mole) and 1000 milliliters of acetic acid were added to a reactor and maintained under a nitrogen atmosphere with stirring. The stirred solution was maintained at 25° C., then 49.03 grams of maleic anhydride (0.50 mole) dissolved in 100 milliliters of acetic acid was added to the reactor and heating to 115° C. commenced. The 115° C. reaction temperature was maintained for 18 hours (64,800 s), then the product was dried under vacuum by rotary evaporation at 120° C. for 30 minutes (1800 s) to a dark brown solid. The crude product was extracted with two 250 milliliter portions of o-dichlorobenzene at 120° C. The combined extracts were maintained at 2° C. for 24 hours (86,400 s) then the light yellow orange colored crystalline product was recovered by filtration and dried under vacuum at 60° C. for 24 hours (86,400 s) to provide 23.1 grams of N-(3-hydroxyphenyl)maleimide. Infrared spectrophotometric analysis of a film sample, nuclear magnetic resonance spectroscopy and mass spectroscopy (m/Z=214) all confirmed the product structure.

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. additionwas added to the reactor
  3. temperatureheating to 115° C.
  4. customThe 115° C. reaction temperature
  5. temperaturewas maintained for 18 hours (64,800 s)
  6. customthe product was dried under vacuum by rotary evaporation at 120° C. for 30 minutes (1800 s) to a dark brown solid
  7. extractionThe crude product was extracted with two 250 milliliter portions of o-dichlorobenzene at 120° C
  8. temperatureThe combined extracts were maintained at 2° C. for 24 hours (86,400 s)
  9. filtrationthe light yellow orange colored crystalline product was recovered by filtration
  10. customdried under vacuum at 60° C. for 24 hours (86,400 s)

Sources & evidence

ORD record
ord-e2927fd783c4410c8680cace4249232b
Source dataset
uspto-grants-1987_07
Patent number
US04680378

Reaction notes

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