반응 #156282

반응 방정식

sodium hydroxide

water ethyl acetate

(2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one

cyclopentylhydrazine hydrochloride

→

5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole

수율 72.7%

용매

acetic acid

반응 조건

후처리

1. 1
   기타The aqueous layer was separated
2. 2
   세척the organic layer was washed with water and saturated brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타The solvent was evaporated under reduced pressure
5. 5
   기타the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

실험 절차

Under a nitrogen atmosphere, to a solution of 1.15 g of (2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one in 9.2 mL of acetic acid was added 1.05 g of cyclopentylhydrazine hydrochloride, followed by stirring at room temperature for 60 hours. The reaction mixture was poured into a mixture of water/ethyl acetate, followed by adjusting to pH 10 with a 6 M aqueous sodium hydroxide solution. The aqueous layer was separated, and then the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 940 mg of 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole.

출처