Ethyl 2,4-dioxovalerate → Ethyl-1-(3-Chloro-4-fluorophenyl)-5-methyl-1H-pyrazole-3-carboxylate

HRID 733147Notes

Reaction equation

HRID 733147 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][NH2:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:11]([O:13][C:14](=[O:21])[C:15](=O)[CH2:16][C:17](=O)[CH3:18])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([CH3:18])[N:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)[N:10]=1)=[O:21])[CH3:12]

Participants

4

Reactant 2

HCID 69208Ethyl 2,4-dioxovalerateHCID 27365753-Chloro-4-fluorophenylhydrazine

Product 1

HCID 57839538Ethyl-1-(3-Chloro-4-fluorophenyl)-5-methyl-1H-pyrazole-3-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-chloro-4-fluorophenylhydrazine (2 g, 12.4 mmol) and ethyl-2,4-dioxovalerate (2.36 g, 14.9 mmol) in ethanol (40 ml) was refluxed for 16 hours, then cooled to room temperature and partitioned between EtOAc and water. The organic layer was washed with saturated bicarbonate, brine solution, dried over sodium sulfate, filtered, concentrated and purified by silica-gel column chromatography using 4% EtOAc in heaxanes to give the product (2.45 g, 71%) as a solid.

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with saturated bicarbonate, brine solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica-gel column chromatography

Sources & evidence

ORD record
ord-2b86ba7b730848abba7b82a6d5aa248d
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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