* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: A solution of the corresponding substituted phenylhydrazine hydrochloride (1 equiv.) and pivaloylacetonitrile (1.2 equiv.) was stirred overnight at 80 °C in ethanol. The solution was extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), filtered, and evaporated to dryness.#10;#10;
79%
With hydrogenchloride In ethanol for 48 h; Reflux
General procedure: A solution of 4-tolyllhydrazine hydrochloride(5.20 g, 33 mmol) and pentylacyl acetonitrile (3.75 g, 30 mmol) in 0.4 M ethanolic solution of HCl(100 mL) was heated under reflux during 48 h. After cooling to room temperature, 1M NaOH wasadded to the mixture until the pH reached 10–11. The mixture was partitioned between water and ethylacetate. The water phase was extracted twice with dichloromethane. The organic phases werecombined and washed with water and brine, then dried with Na2SO4. Evaporation of the solvent invacuo afforded the crude product, which was subjected to recrystallization from ethyl acetate andpetroleum ether to produce compound 25a as a white solid (5.88 g, 86percent yield).
Reference：
[1] Molecules, 2016, vol. 21, # 5,
[2] Molecules, 2014, vol. 19, # 2, p. 2004 - 2028
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 2994 - 3008
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 818 - 823
1-(3-methylphenyl)-5-(4-methylphenyl)-3-(trifluoro-methyl)-1H-pyrazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
In ethanol; for 20h;Heating / reflux;
A solution of 4,4, 4-trifluoro-l- (4-methylphenyl) butane- 1,3-dione (230 mg, 1.00 mmol) and 3-methylphenylhydrazine hydrochloride (174 mg, 1.10 mmol) in ethanol (5 ml) was refluxed under heating for 20 hours. After cooling the reaction mixture, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5-> 90: 10) to give 1- (3-methylphenyl)-5- (4-methylphenyl)-3- (trifluoro- methyl)-lH-pyrazole (298 mg, 94percent) as powders.
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