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

HRID 2108181

Reaction equation

HRID 2108181 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-39949f5565fe45a3ad4bb08b81a51216
Source dataset
uspto-grants-1990_06
Patent number
US04937356

Linked notes

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