Acetonitrile → HCID 18348596, compound

HRID 2268515Notes

Reaction equation

HRID 2268515 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.[C:31]([C:34]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([NH2:60])=[O:59])[CH2:42][C:41]2[C:36](=[C:37]([O:49]C)[C:38]([O:47][CH3:48])=[C:39]([O:45][CH3:46])[C:40]=2[O:43]C)[CH2:35]1)(=[O:33])[NH2:32]>O>[C:31]([C:34]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([NH2:60])=[O:59])[CH2:42][C:41]2[C:40](=[O:43])[C:39]([O:45][CH3:46])=[C:38]([O:47][CH3:48])[C:37](=[O:49])[C:36]=2[CH2:35]1)(=[O:33])[NH2:32]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348523HCID 18348523, compound

Product 1

HCID 18348596HCID 18348596, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (334 mg, 0.610 mmols) was dropwise added to an acetonitrile (2.0 ml) solution of 8-(2-carbamoyl-4,5,6,7-tetramethoxyindan-2-yl)octanamide (103 mg, 0.244 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 out in vacuo and the resulting crude product was purified by silica gel column chromatography (ethyl acetate) followed by recrystallization from ethyl acetate to obtain the entitled compound (35 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 out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9758b0d7a3c44db08f4c56980d103038
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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