Acetylacetone → HCID 13019919, compound

HRID 394797Notes

Reaction equation

HRID 394797 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[CH3:12][C:13](=O)[CH2:14][C:15](=O)[CH3:16]>C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:12])=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 13019919HCID 13019919, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-methoxyphenylhydrazine hydrochloride (118.7 g, 0.68 mol) in 300 ML of glacial acetic acid was added 2,4-pentanedione (68.0 g, 0.68 mol). The resulting solution was stirred at 100° C. for 18 h and then was cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate, filtered through a pad of silica gel and concentrated to afford 131 g (95%) of the title compound, which was used without purification. LRMS (NH4-CI): 203.3 (M+H)+.

Workup

  1. temperaturewas cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa0031edb7834ec393a439f88f730861
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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