4-Methylphenylhydrazine monohydrochloride → 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

HRID 871744ノート

反応式

HRID 871744 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].[OH-].[Na+].Cl.[C:16]1([CH3:24])[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1>CCO.O>[C:16]1([CH3:24])[CH:21]=[CH:20][C:19]([N:22]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:23]2)=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 14798Sodium HydroxideHCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

生成物 1

HCID 668765651-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine収率 57.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 3-oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile (500 mg, 2.8 mmol) (from Example 137A Step 2) in EtOH (10 mL) was added water (7.2 mL) and 1 M NaOH (2.8 mL) followed by p-tolylhydrazine hydrochloride (444 mg, 2.8 mmol) and the solution heated at 80° C. overnight. The solution was cooled to rt, diluted with water and extracted with 2 portions of EtOAc. The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude solid was purified using silica gel chromatography using a gradient of 5-25% EtOAc/hexane to give 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine (452 mg, 57% yield). LC-MS (ESI) m/z 282 (M+H)+

後処理

  1. temperatureThe solution was cooled to rt
  2. extractionextracted with 2 portions of EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude solid was purified

出典と根拠

ORDレコード
ord-44e5f9b1fc894dfd970d4fd6833aa5a0
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

反応ノート

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