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

HRID 1242929
ノート
印刷プレビュー

反応式

HRID 1242929 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1fc583316a6144c18b3de09b89a850a2
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07115750B1

反応ノート

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