Acetic Anhydride → 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl acetate

HRID 257546

Reaction equation

HRID 257546 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12](O)=[O:13])=[CH:4][CH:3]=1.[C:16]([O-])(=[O:18])[CH3:17].[Na+].C(OC(=O)C)(=O)C>O>[C:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:15])[CH:10]=[CH:11][C:12]2=[O:13])=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 1550903(Z)-4-((4-Hydroxyphenyl)amino)-4-oxobut-2-enoic acid

Product 1

HCID 2276844-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl acetateYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a three-neck 1 liter reaction vessel equipped with a condenser, a teflon stirring rod and a thermometer, 97 g (0.49 moles) of N-(4-hydroxyphenyl)maleamic acid, 27.7 g (0.38 moles) of sodium acetate and 400 g of acetic anhydride are added and then heated by using silicone oil. When the reaction solution reaches 70° C. for 2 hours with stirring, the solution is poured into a large amount of distilled water and a great amount of precipitates are formed. The precipitate is taken by filtration and washed several times with distilled water to remove acetic acid, followed by recrystallization from ethanol to give the titled compound. Yield 53%. B.P. 155°-158° C.

Workup

  1. customTo a three-neck 1 liter reaction vessel
  2. customequipped with a condenser
  3. temperatureheated
  4. customa great amount of precipitates
  5. customare formed
  6. filtrationThe precipitate is taken by filtration
  7. washwashed several times with distilled water
  8. customto remove acetic acid
  9. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-996413313eac4b079d48530336575859
Source dataset
uspto-grants-1993_11
Patent number
US05262500

Linked notes

Loading…