Ethyl 2-(methoxyimino)-4-oxopentanoate → Ethyl 3-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylate

HRID 598193

Reaction equation

HRID 598193 reaction equation
CON=[C:4]([CH2:10][C:11](=O)[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1[NH:24][NH2:25]>C(O)(=O)C.C(OCC)(=O)C>[CH3:12][C:11]1[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:24]([C:17]2[C:16]([Cl:15])=[CH:21][C:20]([Cl:22])=[CH:19][C:18]=2[Cl:23])[N:25]=1

Participants

5

Reactant 2

HCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoateHCID 3014122(2,4,6-Trichlorophenyl)hydrazine monohydrochloride

Product 1

HCID 67267631Ethyl 3-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylateYield 42%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of ethyl 2-(methoxyimino)-4-oxopentanoate (2.00 g, 10.7 mmol) and 2,4,6-trichlorophenylhydrazine hydrochloride (3.39 g, 16.0 mmol) in acetic acid (40 ml) and 2-methoxuethanol (20 ml) was stirred for 20 h at 105° C. The solvent was under vacuum and the residue was dissolved in ethyl acetate. The organic solution was washed with 0.2N HCl and water, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with 10% ethyl acetate/n-hexane to give the title compound (1.50 g, 42%).

Workup

  1. washThe organic solution was washed with 0.2N HCl and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 10% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d7df74e885d3482785c853c60c336a87
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Linked notes

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