2,5-Hexanedione → HCID 4763633, compound

HRID 545247Notes

Reaction equation

HRID 545247 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[CH3:10][C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15]>C(O)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[CH3:10])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 233594-Bromo-3-methylaniline

Product 1

HCID 4763633HCID 4763633, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (30 mL) solution of 9.30 g of 4-bromo-3-methylaniline and 6.85 g of 2,5-hexanedione was stirred at 80° C. for 5 hours. The reaction liquid was concentrated, aqueous saturated sodium hydrogencarbonate solution was added thereto, extracted with ethyl acetate, washed with saturated saline water, and dried with anhydrous magnesium sulfate. This was filtered through silica gel column chromatography (ethyl acetate), the solvent was concentrated, hexane was added to it, and the formed solid was collected to obtain 10.90 g of the entitled compound as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. additionaqueous saturated sodium hydrogencarbonate solution was added
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated saline water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationThis was filtered through silica gel column chromatography (ethyl acetate)
  8. concentrationthe solvent was concentrated
  9. additionhexane was added to it
  10. customthe formed solid was collected

Sources & evidence

ORD record
ord-480660657cc7499cb756748594899d11
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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