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Methyl iodide → 7-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871975
ノート
印刷プレビュー

反応式

HRID 871975 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([N:12](CO)[C:13]([CH3:21])([CH3:20])[C:14](=[O:19])[N:15]3[CH3:18])=[CH:10][CH:9]=2)[CH:7]=1.CI.[C:27](=[O:30])([O-])[O-].[K+].[K+].[C:33](OCC)(=O)C>CN(C)C=O.O.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:33])=[C:6]([C:8]2[C:17]([CH2:27][OH:30])=[C:16]3[C:11]([NH:12][C:13]([CH3:21])([CH3:20])[C:14](=[O:19])[N:15]3[CH3:18])=[CH:10][CH:9]=2)[CH:7]=1
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

8

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 867022207-(5-chloro-2-hydroxyphenyl)-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

生成物 1

HCID 576717857-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one収率 96%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 7-(5-chloro-2-hydroxyphenyl)-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 12-1, 1.36 g, 3.92 mmol), methyl iodide (244 μL, 3.92 mmol), and potassium carbonate (1.08 g, 7.81 mmol) was suspended in anhydrous N,N-dimethylformamide (20 mL) and stirred at 50° C. for 1 hour. After cooling down, ethyl acetate (70 mL), diethylether (70 mL), and water (150 mL) were added and partitioned. The organic layer was washed with water (100 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.36 g) as a pale yellow amorphous product. (Yield 96%)

後処理

  1. temperatureAfter cooling down
  2. custompartitioned
  3. washThe organic layer was washed with water (100 mL) and saturated brine (50 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-7c888f394da64d22961bdf8a42e680d2
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975256B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート