4-Methylphenylhydrazine monohydrochloride → 3-(4-fluorophenyl)-5-methyl-1H-indole

HRID 717753노트

반응식

HRID 717753 반응식
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]=O)=[CH:14][CH:13]=1.[OH-].[K+]>C(O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:6]3[C:5](=[CH:4][CH:3]=[C:2]([CH3:10])[CH:7]=3)[NH:8][CH:19]=2)=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 14797Potassium HydroxideHCID 111263222-(4-fluorophenyl)acetaldehyde

생성물 1

HCID 103763663-(4-fluorophenyl)-5-methyl-1H-indole수율 47%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of p-tolyl hydrazine hydrochloride (3 g, 0.0189 mol), 4-fluorophenyl acetaldehyde (3 g, 0.0227 mol) and ethanol (50 mL) was heated at 80° C. for 1 h. After completion of reaction (monitored by TLC), the mixture was cooled to RT, basified with potassium hydroxide solution, and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by column chromatography (15% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a brown colored oil (2 g, 47% yield).

후처리

  1. customAfter completion of reaction (monitored by TLC)
  2. temperaturethe mixture was cooled to RT
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography (15% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

출처 및 근거

ORD 기록
ord-39d2dc1af5084f7799e431495006ce26
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193728B2

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