Phosphoric Acid → 4-(4-Ethylphenylmethyl)pyrazole

Temperature

0 °C

The above 3,5-diamino-4-(4-ethylphenylmethyl)pyrazole (1.30 g) was added to 50% aqueous phosphoric acid solution (19 ml), and further added thereto was water (10 ml). The mixture was cooled to 0° C., and thereto was added dropwise an aqueous solution (4 ml) of sodium nitrite (912 mg). The mixture was stirred at the same temperature for 30 minutes, and further stirred at room temperature for 4 hours. The reaction mixture was cooled again to 0° C., 10% aqueous sodium hydroxide solution was added thereto to adjust pH of the reaction mixture to 7. The mixture was extracted with ethyl acetate, washed successively with water and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0-90:10) to give the desired 4-(4-ethylphenylmethyl)pyrazole (414 mg) as a pale brown semisolid. APCI-Mass m/Z 187 (M+H).

1. additionfurther added
2. stirringfurther stirred at room temperature for 4 hours
3. temperatureThe reaction mixture was cooled again to 0° C.
4. extractionThe mixture was extracted with ethyl acetate
5. washwashed successively with water and brine
6. dry with materialdried over magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:0-90:10)

ORD record

ord-671d689ecc794ba4a5d4c1ae7ae36be1

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2