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

HRID 2268517
Notes
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Reaction equation

HRID 2268517 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-729ac23ac3bb4e26b2814a10865845a7
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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