Isoamyl Nitrite → Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

HRID 1744470Notes

Reaction equation

HRID 1744470 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].N(OCCC(C)C)=O>O1CCCC1>[F:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[CH:2]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[N:5]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 688689ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 14994516Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylateYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-amino-1-(4-fluorophenyl)pyrazole-4-carboxylate (15 g) was dissolved in tetrahydrofuran (150 ml) and isoamyl nitrite (21.2 g) was added. The mixture was stirred at a refluxing temperature for 2 h. After cooling, the precipitated crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (10.6 g).

Workup

  1. temperatureAfter cooling
  2. customthe precipitated crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-8a4f22ce48f446dca7089e1234ba5bfe
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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