Isoamyl Nitrite → HCID 15407381, compound

HRID 850067Notes

Reaction equation

HRID 850067 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:9]([C:18]#[N:19])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].N(OCCC(C)C)=O>O1CCCC1>[C:18]([C:9]1[CH:8]=[C:7]([N:6]2[CH:2]=[C:3]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:4]=[N:5]2)[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH:15]([CH3:17])[CH3:16])#[N:19]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 15406550HCID 15406550, compound

Product 1

HCID 15407381HCID 15407381, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, to a solution (16 ml) of ethyl 5-amino-1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylate (1.64 g) obtained in Example 1 in tetrahydrofuran was added isoamyl nitrite (1.75 g) with stirring, and the mixture was refluxed under heating for 1.5 hours. After the completion of the reaction, the solvent was evaporated under reduced pressure and the obtained residue was recrystallized from ethyl alcohol to give 1.38 g of ethyl 1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylate, melting point 138-139° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1.5 hours
  3. customAfter the completion of the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. customthe obtained residue was recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-52b2b97b3c45437b871223686628f8e3
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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