Ethanol → 4-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline

HRID 588870노트

반응식

HRID 588870 반응식
[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:12]C(=O)C)=[C:4]([O:16][CH3:17])[CH:3]=1.[OH-].[K+].C(O)C>O>[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:9][CH2:10]2)=[CH:6][C:5]([NH2:12])=[C:4]([O:16][CH3:17])[CH:3]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 90455914N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamide

생성물 1

HCID 904558234-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline수율 67.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of N-(4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)acetamide (820 mg, 3.23 mmol), KOH (1.8 g, 32.3 mmol), ethanol (40 mL) and water (20 mL) was stirred at reflux for 12 h. The reaction mixture was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=20:1) to afford the desired product (460 mg, 67% yield). ESI-MS m/z: 212.4[M+H]+.

후처리

  1. temperatureat reflux for 12 h
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=20:1)

출처 및 근거

ORD 기록
ord-0056386f1ecc487cbeac5491d8ced0cf
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227978B2

반응 노트

불러오는 중…