Acetic Anhydride → 1H-Pyrrole-2,5-dione, 1-(3-ethynylphenyl)-

HRID 478047

Reaction equation

HRID 478047 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([C:15]#[CH:16])[CH:12]=[CH:13][CH:14]=1.C(OC(=O)C)(=O)C>O.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[C:15]([C:11]1[CH:10]=[C:9]([N:8]2[C:4](=[O:5])[CH:3]=[CH:2][C:1]2=[O:7])[CH:14]=[CH:13][CH:12]=1)#[CH:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 7100601H-Pyrrole-2,5-dione, 1-(3-ethynylphenyl)-Yield 80.1%

Reagents, catalysts & solvents 2

HCID 62601Nickel acetate tetrahydrateCatalystHCID 962WaterSolvent

Procedure

Maleic anhydride (79.6 g, 0.81 mole) was added to a solution of distilled 3-aminophenylacetylene (95.1 g, 0.81 mole) dissolved in 500 mL of dry N,N'-dimethylacetamide (DMAc) at 5°-10° C. After addition, another 300 mL of DMAc was added and the mixture stirred at room temperature for two hours. Nickel acetate tetrahydrate (0.8 g) and acetic anhydride (300 mL) were added to the reaction mixture and stirring was continued for 12 hours at room temperature to affect cyclodehydration. The crude product was isolated by precipitation in water and recrystallized from methanol to provide N-(3-ethynylphenyl)maleimide (128 g, 80% yield) as a yellow crystalline solid, mp 129°-131° C. Elemental analysis calculated for C12H7NO2 : C, 73.09%; H, 3.58%; N, 7.10%. Found: C, 72.94%; H, 3.61%; N, 7.04%.

Workup

  1. additionAfter addition
  2. stirringstirring
  3. waitwas continued for 12 hours at room temperature
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c7149af7e208494380914fed1a944b35
Source dataset
uspto-grants-1989_12
Patent number
US04889912

Linked notes

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