4-Fluorophenylhydrazine hydrochloride → HCID 19886090, compound

HRID 654777Notes

Reaction equation

HRID 654777 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:2]=1.Cl.[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1>O1CCOCC1.C(O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:17])=[CH:2][CH:3]=3)=[CH:8][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 595052Ethyl 2,4-dioxo-4-(p-tolyl)butanoate

Product 1

HCID 19886090HCID 19886090, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 4-(4-tolyl)-2,4-dioxobutanoate (4.7 g) and 4-fluorophenylhydrazine hydrochloride (3.6 g) in dioxane (35 ml) and ethanol (35 ml) was refluxed for 5 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The oily residue (8 g) was purified.by column chromatography on silica gel (130 g) eluting with chloroform to give an oil of ethyl 1-(4-fluorophenyl)-5-(4-tolyl)pyrazole-3-carboxylate (2.7 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. washeluting with chloroform

Sources & evidence

ORD record
ord-e9c98eacbb4a4fa49693d26d9df75d47
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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