Ceric ammonium nitrate → HCID 71743958, compound

HRID 2277626Notes

Reaction equation

HRID 2277626 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6](CC1C=CC(OC)=CC=1)[C:5]2([CH3:22])[CH3:21].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.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2([CH3:22])[CH3:21]

Participants

6

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 86685945HCID 86685945, compound

Product 1

HCID 71743958HCID 71743958, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-fluoro-2-(4-methoxy-benzyl)-3,3-dimethyl-2,3-dihydro-isoindol-1-one (3.8 g, 12.7 mmol) in MeCN (80 ml) and H2O (40 mL) was added CAN (20.9 g, 38.1 mmol) at 0° C. After stirring for 2 hours at 0° C., the reaction mixture was diluted with EtOAc and washed with brine. The organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to provide a crude product, which was purified by column chromatography to give tile product (1.03 g, yield 45%) as a solid.

Workup

  1. washwashed with brine
  2. customThe organic layers were dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo
  5. customto provide a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b4e64c93dc9441f78fc5e43e9cb3136a
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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