HCID 17960600, compound → HCID 17960601, compound

HRID 2223744Notes

Reaction equation

HRID 2223744 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([C:8]2[NH:9][CH2:10][CH2:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1>CN(C)C=O.C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 17960600HCID 17960600, compound

Product 1

HCID 17960601HCID 17960601, compoundYield 28.8%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the title compound of Example 1, Step A (0.35 g, 1.71 mmol) in dimethylformamide (20 mL) was added activated manganese dioxide (4.46 g, 51.3 mmol) and the mixture was heated at 120° C. for 2 hours. After cooling, the mixture was diluted with ethyl acetate, filtered through a pad of Celite® and washed three times with water and once with a saturated solution of sodium chloride. The organic phase was dried (magnesium sulfate), concentrated and purified by flash column chromatography (silica gel, 60% then 80% ethyl ether in hexanes then ethyl ether) to give the title compound of Step A (0.1 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through a pad of Celite®
  3. washwashed three times with water
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, 60%

Sources & evidence

ORD record
ord-f5c1fefdcc5b4486a58e3052e5941d4a
Source dataset
uspto-grants-2008_05
Patent number
US07375232B2

Reaction notes

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