Ethyl Acetoacetate → HCID 22347339, compound

HRID 432503Notes

Reaction equation

HRID 432503 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=O)[CH2:2][C:3](C)=O.Cl.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1>C(O)(=O)C>[CH2:8]([O:7][C:1]1[N:18]([C:15]2[CH:16]=[CH:17][C:12]([Br:11])=[CH:13][CH:14]=2)[N:19]=[CH:3][CH:2]=1)[CH3:9]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 22347339HCID 22347339, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl acetoacetate (3.49 g, 0.02684 mol) and 4-bromophenylhydrazine hydrochloride (6.00 g, 0.02684 mol) were refluxed in acetic acid (50 mL) for 4 hours. The precipitate was removed by filtration, the filtrate concentrated under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase to yield 1-(4-bromophenyl)-1H-5-pyrazolyl ethyl ether (2.63 g, 0.00936 mol) as an off-white solid.

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe residue purified by flash chromatography on silica

Sources & evidence

ORD record
ord-595ac1aab63841178bc200dc1f8b22f3
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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