Isoamyl Nitrite → 1-(2,4-Difluorophenyl)-N-ethyl-4-nitroso-1H-pyrazol-5-amine

HRID 383568Notes

Reaction equation

HRID 383568 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][CH3:16])=[CH:12][CH:11]=[N:10]1.[N:17](OCCC(C)C)=[O:18]>CCOC(C)=O.CCO.Cl.CC(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][CH3:16])=[C:12]([N:17]=[O:18])[CH:11]=[N:10]1

Participants

7

Reactant 2

HCID 8053Isoamyl NitriteHCID 671980121-(2,4-difluorophenyl)-N-ethyl-1H-pyrazol-5-amine

Product 1

HCID 866529991-(2,4-Difluorophenyl)-N-ethyl-4-nitroso-1H-pyrazol-5-amine

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2,4-difluorophenyl)-N-ethyl-1H-pyrazol-5-amine (1.15 g, 5.16 mmol) in 4.0 mL of EtOAc, 2.0 mL of EtOH and 4.0 mL of 5-6 N HCl in 2-propanol was cooled in an ice/brine bath and treated with isoamyl nitrite (0.70 mL, 5.28 mmol) drop wise. After stirring at this temperature for 15 min, the reaction was quenched by the addition of 28-30% NH4OH solution and EtOAc, forming a deep blue solution. The EtOAc layer was separated, washed with brine, dried and concentrated to afford the title compound as a brown crystalline solid. MS (ES+): 253.1 (M+H)+.

Workup

  1. customthe reaction was quenched by the addition of 28-30% NH4OH solution and EtOAc
  2. customforming a deep blue solution
  3. customThe EtOAc layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-45817093c08f4bceb010132d064dbc86
Source dataset
uspto-grants-2013_02
Patent number
US08367671B2

Reaction notes

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