HCID 12550574, compound → 3-Anilino-1-phenyl-1H-pyrrole-2,5-dione

HRID 845321Notes

Reaction equation

HRID 845321 reaction equation
[NH:1]([CH:8]1[CH2:13][C:12](=[O:14])[NH:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[NH:1]([C:8]1[C:9](=[O:10])[N:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12](=[O:14])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12550574HCID 12550574, compound

Product 1

HCID 2885553-Anilino-1-phenyl-1H-pyrrole-2,5-dioneYield 45.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1.98 g (7.5 mmol) of the anilinosuccinimide prepared in Example 1 above and 1.96 g (22.5 mmol) of MnO2 in 45 mL of toluene is refluxed for six hours. The mixture is filtered, while hot, and the resulting solid is heated in another 50 mL of boiling toluene and filtered again while hot. Cooling the combined toluene filtrates gives 450 mg of the title product as yellow-orange needles. Concentration of the toluene solution gives another 360 mg; m.p. 228°-233° C. (lit (7) m.p. 230°-230.5° C.).

Workup

  1. filtrationThe mixture is filtered
  2. temperaturewhile hot, and the resulting solid is heated in another 50 mL of boiling toluene
  3. filtrationfiltered again while hot
  4. temperatureCooling the combined toluene filtrates

Sources & evidence

ORD record
ord-a3edee9e4a754af5af7a7374d1964aa7
Source dataset
uspto-grants-1988_07
Patent number
US04757146

Reaction notes

Loading…