Hydrochloric Acid → 5-Amino-4-nitroso-1-phenylpyrazole

HRID 1693503Notes

Reaction equation

HRID 1693503 reaction equation
[C:1]1([N:7]2[C:11]([NH2:12])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[N:14](OC(C)(C)C)=[O:15]>CCO>[N:14]([C:10]1[CH:9]=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]=1[NH2:12])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 700061-Phenylpyrazol-5-ylamine

Product 1

HCID 107501065-Amino-4-nitroso-1-phenylpyrazoleYield 60.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-phenyl-2H-pyrazol-3-ylamine (250 mg, 1.57 mmol) in EtOH (3 mL) is added HCl (4N in dioxane, 1.15 mL, 4.6 mmol). The mixture is then cooled down to −10° C., tert-butyl nitrite (178 mg, 1.73 mmol) is added drop wise. After addition, the mixture is stirred at 0° C. for 1 h. The precipitate is collected by filtration to provide 4-nitroso-2-phenyl-2H-pyrazol-3-ylamine (180 mg, 60%) as yellow solid.

Workup

  1. additionAfter addition
  2. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-3213cd3c01f1486f8e683f16d8e94c13
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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