Ceric ammonium nitrate → HCID 71743861, compound

HRID 2277633Notes

Reaction equation

HRID 2277633 reaction equation
COC1C=CC(C[N:8]2[C:16]([CH3:18])([CH3:17])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:19]#[N:20])[CH:14]=3)[C:9]2=[O:21])=CC=1.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+]>CC#N.O>[CH3:17][C:16]1([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]#[N:20])[CH:14]=2)[C:9](=[O:21])[NH:8]1

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 86685949HCID 86685949, compound

Product 1

HCID 71743861HCID 71743861, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-methoxy-benzyl)-3,3-dimethyl-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile (3.5 g, 11.42 mmol) in MeCN (70 mL) was added CAN (18.79 g, 34.27 mmol) in 30 mL of water at 0° C. The resulting reaction mixture was stirred at 0° C. for 1 hour until all the starting material was consumed. The reaction mixture was extracted between water and EtOAc and the combined organic layers were dried over anhy. MgSO4, filtered, and concentrated under reduced pressure to give a crude product which was purified by column chromatography to afford the title compound (1.06 g, 49.8%) as a solid.

Workup

  1. customThe resulting reaction mixture
  2. customwas consumed
  3. extractionThe reaction mixture was extracted between water and EtOAc
  4. customthe combined organic layers were dried over anhy
  5. filtrationMgSO4, filtered
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude product which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5b10634c20c54b97988785da3f0111ae
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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