HCID 118005547, compound → HCID 118005559, compound

HRID 1478503Notes

Reaction equation

HRID 1478503 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:19]([C:21]3[N:25]([CH3:26])[C:24]([CH3:27])=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1>[O-2].[O-2].[Mn+4].O1CCOCC1>[Cl:1][C:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:21]3[N:25]([CH3:26])[C:24]([CH3:27])=[N:23][CH:22]=3)=[O:20])[CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 118005547HCID 118005547, compound

Product 1

HCID 118005559HCID 118005559, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a flask containing (2,4-dichloro-3-phenylquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol (520 mg, 1.31 mmol, Intermediate 18: step a) was added 1,4-dioxane (12 mL) followed by manganese dioxide (475 mg, 5.46 mmol). The mixture was heated to reflux for 3.25 hours and then the contents were filtered through a Celite® pad, while still warm, and the Celite® pad was rinsed with warm THF. The effluent was concentrated under reduced pressure to provide the title compound as an off white foam.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3.25 hours
  3. filtrationthe contents were filtered through a Celite® pad
  4. temperaturewhile still warm
  5. washthe Celite® pad was rinsed with warm THF
  6. concentrationThe effluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-575c87bccb864585a3ea290a16e73052
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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