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

HRID 2268517
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HRID 2268517 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-729ac23ac3bb4e26b2814a10865845a7
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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