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

HRID 973698Notes

Reaction equation

HRID 973698 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 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of ethyl 5-amino-1-(4-fluoro-phenyl)-1H-pyrazole-4-carboxylate (7.48 g, 30.0 mmole), prepared as described in Preparation A, above, and isopentyl nitrite (7.03 g, 60.0 mmole) in 80 ml of tetrahydrofuran was refluxed for twenty-four hours and then evaporated in vacuo. The residue was triturated with 50 ml of methanol and filtered to furnish 5.18 g (74% yield) of off-white solid. The sample was recrystallized from ethanol, m.p. 119-21° C.

Workup

  1. customprepared
  2. customas described in Preparation A
  3. customevaporated in vacuo
  4. customThe residue was triturated with 50 ml of methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fa8c008662a24ea7bf6e01180a52dfd3
Source dataset
uspto-grants-1991_11
Patent number
US05064851

Reaction notes

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