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

HRID 241984

反応式

HRID 241984 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
135 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b9c725f3ad864d63917729977f935ea6
出典データセット
uspto-grants-2014_02
特許番号
US08653079B2

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