Ethyl 3-(2-fluorophenyl)-3-oxopropanoate → 2,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

HRID 241984

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HRID 241984 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][C:10]([O:12]CC)=O.Cl.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][NH2:25]>C(O)(=O)C>[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[C:10](=[O:12])[CH2:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:25]1

참가 물질

4

반응물 2

HCID 296342Ethyl 3-(2-fluorophenyl)-3-oxopropanoateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

생성물 1

HCID 671115152,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
135 °C

실험 절차

Ethyl 3-(2-fluorophenyl)-3-oxopropanoate (2.5 g, 12 mmol) and 2-fluorophenyl hydrazine hydrochloride (1.5 g, 12 mmol, 1.0 equiv) were dissolved in acetic acid (24 mL) and placed into a preheated oil bath at 120° C. for 3 hours and then heated for an additional 2 hours at 135° C. The mixture was cooled to ambient temperature, concentrated in vacuo and then concentrated once from toluene (1×25 mL). The residue was suspended in dichloromethane, filtered and the solid was washed once with dichloromethane and dried in vacuo, providing the titled compound. The resulting filtrate was concentrated in vacuo and purified by silica gel gradient chromatography (100:0 to 65:35; hexanes:ethyl acetate), providing additional titled compound as a light brown solid.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. concentrationconcentrated once from toluene (1×25 mL)
  4. filtrationfiltered
  5. washthe solid was washed once with dichloromethane
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-b9c725f3ad864d63917729977f935ea6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653079B2

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