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Water → Acetamide, N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl)-

HRID 1242929
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HRID 1242929 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].CI.O.[C:19](OCC)(=O)C>O1CCCC1>[CH3:19][N:4]([C:5]1[CH:14]=[CH:13][C:12]2[C:11](=[O:15])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=1)[C:1](=[O:3])[CH3:2]
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참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

생성물 1

HCID 10536752Acetamide, N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl)-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

6-Acetamido-1-tetralone (13.7 g, 67.4 mmol) was dissolved in tetrahydrofuran (40 ml). Sodium hydride(oil)(2.40 g, 101 mmol) was added to the solution, which was refluxed with heating for 2.5 hours. After cooling, methyl iodide(20 ml)was added to the reaction mixture, which was stirred at 40° C. for 15 hours. The reaction mixture was poured into a cold water, and extraction was conducted using ethyl acetate. The extract was washed with 1N hydrochloric acid and 1 N aqueous sodium hydroxide solution. The ethyl acetate layer was concentrated. The residue was purified by alumina column chromatography (development solvent; ethyl acetate:n-hexane=50:50 ˜100:0). The eluent was concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-diisopropyl ether, to give the titled compound(8.3 g).

후처리

  1. temperaturewas refluxed
  2. temperaturewith heating for 2.5 hours
  3. temperatureAfter cooling
  4. washThe extract was washed with 1N hydrochloric acid and 1 N aqueous sodium hydroxide solution
  5. concentrationThe ethyl acetate layer was concentrated
  6. customThe residue was purified by alumina column chromatography (development solvent; ethyl acetate:n-hexane=50:50 ˜100:0)
  7. concentrationThe eluent was concentrated under reduced pressure
  8. customThe resulting residue was recrystallized from ethyl acetate-diisopropyl ether

출처 및 근거

ORD 기록
ord-1fc583316a6144c18b3de09b89a850a2
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07115750B1

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