Phenylhydrazine hydrochloride → 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

HRID 1917888ノート

反応式

HRID 1917888 の反応式
O=[C:2]([C:6]1([C:9]([F:12])([F:11])[F:10])[CH2:8][CH2:7]1)[CH2:3][C:4]#[N:5].Cl.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO.O>[C:14]1([N:20]2[C:4]([NH2:5])=[CH:3][C:2]([C:6]3([C:9]([F:10])([F:11])[F:12])[CH2:8][CH2:7]3)=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 2

HCID 60962Phenylhydrazine hydrochlorideHCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

生成物 1

HCID 668765051-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine収率 43.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
90 °C

実験手順

To 3-oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile (230 mg, 1.3 mmol) in EtOH (5 mL, 200 proof) was added H2O (3.7 mL), 1NaOH(aq) (1.3 mL), and phenylhydrazine hydrochloride (188 mg, 1.3 mmol) and the mixture heated at 90° C. overnight. After cooling to room temperature, the mixture was diluted with H2O, extracted with EtOAc, the org layer concentrated in vacuo, and purified by column chromatography (5-25% EtOAc/hexanes) to give 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine (150 mg, 0.56 mmol, 43%). LC-MS (ESI) m/z 268 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. concentrationthe org layer concentrated in vacuo
  4. custompurified by column chromatography (5-25% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8d96f4eef52e4f47affe6d344f222609
出典データセット
uspto-grants-2013_12
特許番号
US08618289B2

反応ノート

読み込み中…