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Acetonitrile → N-Methyl-2-(8-hydroxyoctyl)-5,6-dimethoxy-4,7-dioxo-2-indancarboxamide

HRID 2268517
ノート
印刷プレビュー

反応式

HRID 2268517 の反応式
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(#N)C.[CH3:31][NH:32][C:33]([C:35]1([CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][OH:60])[CH2:43][C:42]2[C:37](=[C:38]([O:50]C)[C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[C:41]=2[O:44]C)[CH2:36]1)=[O:34]>O>[CH3:31][NH:32][C:33]([C:35]1([CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][OH:60])[CH2:43][C:42]2[C:41](=[O:44])[C:40]([O:46][CH3:47])=[C:39]([O:48][CH3:49])[C:38](=[O:50])[C:37]=2[CH2:36]1)=[O:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348606N-Methyl-2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxamide

生成物 1

HCID 18348530N-Methyl-2-(8-hydroxyoctyl)-5,6-dimethoxy-4,7-dioxo-2-indancarboxamide収率 44.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A water (1.0 ml) solution of CAN (828 mg, 1.51 mmols) was dropwise added to an acetonitrile (5.0 ml) solution of N-methyl-2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxamide (255 mg, 0.602 mmols), with cooling with ice, and stirring was continued for 15 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried. The solvent was evaporated in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2) followed by recrystallization from ethyl acetate to obtain the entitled compound (106 mg) as crystals.

後処理

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. customdried
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2)
  7. customfollowed by recrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-729ac23ac3bb4e26b2814a10865845a7
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326369B1

反応ノート

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