1,4-Dioxane → HCID 22141372, compound

HRID 1826504Notes

Reaction equation

HRID 1826504 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](C(=NN)C)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:14]1([CH2:20][CH2:21][CH2:22][N:23]2[CH2:27][C:26](=O)[CH2:25][C:24]2=[O:29])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O:30]1[CH2:35][CH2:34]OCC1>[O-2].[Mn+4].[O-2]>[CH3:27][C:26]1([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH:34]2[CH:25]1[C:24](=[O:29])[N:23]([CH2:22][CH2:21][CH2:20][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:35]2=[O:30]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 785070HCID 785070, compoundHCID 22141363HCID 22141363, compound

Product 1

HCID 22141372HCID 22141372, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

To a solution of 1-(3-nitrophenyl)-1-ethanone hydrazone (Preparation 135, 100 g, 0.56 mol) in dioxan (1 l) was added manganese (IV) oxide (200 g, 2.3 mol) and the reaction mixture was stirred at room temperature for 30 min. The suspension was filtered through Celite™ washing with dioxan (ca. 200 ml). 1-(3-Phenylpropyl)-1H-pyrrole-2,4-dione (Preparation 80, 110 g, 0.54 mol) was added to the filtrate and the reaction mixture was stirred at room temperature for 4 h before heating under reflux for 16 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was triturated in methanol (500 ml) and the precipitate was collected by filtration to afford the title compound as a white crystalline solid (121 g, 65%).

Workup

  1. filtrationThe suspension was filtered through Celite™
  2. washwashing with dioxan (ca. 200 ml)
  3. stirringthe reaction mixture was stirred at room temperature for 4 h
  4. temperaturebefore heating
  5. temperatureunder reflux for 16 h
  6. temperatureThe reaction mixture was cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated in methanol (500 ml)
  9. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b8000712a1f741ce91c030ec1323bf6a
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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