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

HRID 388861Notes

Reaction equation

HRID 388861 reaction equation
C1(C)C=CC=CC=1.CS(O)(=O)=O.[C:13]1(=[O:19])[O:18][C:16](=O)[CH:15]=[CH:14]1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](N)[CH:23]=1.C([N:31](CC)CC)C>>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:15]2[C:16]([NH:31][C:13](=[O:19])[CH:14]=2)=[O:18])[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 108243-Methoxyaniline

Product 1

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

Procedure

Toluene (100 mL), triethylamine (10 g), methanesulfonic acid (15 g) were placed into a 500 ml, single-neck flask. Maleic anhydride (21.0 g, 214 millimoles) was dissolved into this mixture. This mixture was stirred magnetically at room temperature and m-anisidine (24.67 g, 200 millimoles) was then added drop-wise over a twenty minute period. A Dean-Stark trap and condenser were attached and the mixture was refluxed for three hours. A total of 3.7 ml of water was collected in the trap. The mixture was cooled to room temperature and the upper (toluene) phase was decanted off. The lower phase was extracted with 6×70 ml portions of fresh toluene. The collected toluene phase was passed over 27 grams of silica gel. The toluene was removed on a rotary evaporator to yield 27.3 g (67% of theory) of a clear yellow liquid. The product crystallized to a solid upon standing at room temperature. The solid melted at 75-76.5° C.

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. customA total of 3.7 ml of water was collected in the trap
  3. temperatureThe mixture was cooled to room temperature
  4. customthe upper (toluene) phase was decanted off
  5. extractionThe lower phase was extracted with 6×70 ml portions of fresh toluene
  6. customThe toluene was removed on a rotary evaporator
  7. customto yield 27.3 g (67% of theory) of a clear yellow liquid
  8. customThe product crystallized to a solid
  9. customupon standing at room temperature

Sources & evidence

ORD record
ord-ec7bbaddd49f44bd916aa50a947d9ab9
Source dataset
uspto-grants-2013_02
Patent number
US08378017B2

Reaction notes

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