Isoamyl Nitrite → Ethyl 1-(4-fluorophenyl)-3-methylpyrazole-4-carboxylate

HRID 1744468Notes

Reaction equation

HRID 1744468 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O-:15])=[O:14])[C:10]([CH3:16])=[N:9]2)=[CH:4][CH:3]=1.N(O[CH2:20][CH2:21]C(C)C)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:20][CH3:21])=[O:14])[C:10]([CH3:16])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 11430Potassium CarbonateHCID 867599491-(4-Fluorophenyl)-3-methylpyrazole-4-carboxylate

Product 1

HCID 22228060Ethyl 1-(4-fluorophenyl)-3-methylpyrazole-4-carboxylateYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (50 ml) containing ethyl 5-amino]1-(4-fluorophenyl)-3-methylpyrazole-4-carboxylate (10.5 g) was added isoamyl nitrite (14 g) and the mixture was stirred at a refluxing temperature for 2 h. The mixture was treated with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. n-Hexane was added to the obtained residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (7.8 g), melting point: 103–104° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. additionn-Hexane was added to the obtained residue
  5. customcrystallization
  6. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-3901f106269442839ce07544774920b5
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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