2,5-Hexanedione → HCID 43806226, compound

HRID 2088464Notes

Reaction equation

HRID 2088464 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[CH2:10]([CH2:14][C:15](=O)[CH3:16])[C:11]([CH3:13])=O>CCO.Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([N:7]2[C:15]([CH3:16])=[CH:14][CH:10]=[C:11]2[CH3:13])[CH:8]=1

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 27348055-Bromo-o-toluidine

Product 1

HCID 43806226HCID 43806226, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution 5-bromo-2-methyl aniline (6.38 g, 36.74 mmol) in EtOH (30 ml) was added acetonyl acetone (5.0 ml, 42.62 mmol) and one drop of conc. aqueous HCl. The mixture was heated at reflux for 18 h and then cooled. Solvent was evaporated to dryness under reduced pressure and the residue was partitioned between water and EtOAc. The organic layer was separated and washed with water and brine dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/8:2) gave 5.8 g of 1-(5-bromo-2-methyl-phenyl)-2,5-dimethyl-1H-pyrrole (60%) as a clear oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. customSolvent was evaporated to dryness under reduced pressure
  5. customthe residue was partitioned between water and EtOAc
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure
  11. customPurification of the residue by flash chromatography (hex:EtOAc/8:2)

Sources & evidence

ORD record
ord-8fa8ea46db214686a96f1d956892eb65
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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