Carbon Dioxide → 3-(3-Methoxyphenyl)-1H-pyrrole-2,5-dione

HRID 371127Notes

Reaction equation

HRID 371127 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5](N)[CH:4]=1.N([O-])=O.[Na+].[C:14]1(=[O:20])[NH:18][C:17](=[O:19])[CH:16]=[CH:15]1.C(=O)=O.C([O-])(=O)C.[Na+]>Cl.O.CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:16]2[C:17]([NH:18][C:14](=[O:20])[CH:15]=2)=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 108243-MethoxyanilineHCID 10935MaleimideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 212246183-(3-Methoxyphenyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A 61.5 g portion of m-anisidine in 150 ml of 12N hydrochloric acid and 150 ml of water was cooled in an ice-salt bath. A 35 g portion of sodium nitrite in 80 ml of water was added dropwise, with stirring over 1/2 hour. A solution of 48.5 g of maleimide in 400 ml of acetone was added together with 50 g of dry-ice. A 125 g portion of sodium acetate was added, followed immediately by 12.75 g of cupric chloride dihydrate. The mixture was allowed to stand 18 hours, then the solid was collected and dried. A 90 g portion of this solid and 51 g of 2,4-lutidine in 250 ml of isopropanol was heated on a steam bath for 1/2 hour, then poured into 1200 ml of water. The solid was collected, dried and then recrystallized, first from isopropanol then from ethyl acetate:ethanol, giving 29.0 g of 2-(m-methoxyphenyl)maleimide as yellow crystals.

Workup

  1. waitto stand 18 hours
  2. customthe solid was collected
  3. customdried
  4. temperatureA 90 g portion of this solid and 51 g of 2,4-lutidine in 250 ml of isopropanol was heated on a steam bath for 1/2 hour
  5. additionpoured into 1200 ml of water
  6. customThe solid was collected
  7. customdried
  8. customrecrystallized, first from isopropanol

Sources & evidence

ORD record
ord-3af07a6b78da438b969c007fc1ec6c31
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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