Ceric ammonium nitrate → HCID 21919202, compound

HRID 1245209Notes

Reaction equation

HRID 1245209 reaction equation
C[O:2][C:3]1[C:4]([CH3:41])=[C:5]([C:32]([O:39]C)=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[CH2:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[O:12])=[C:9]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:8]=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+]>C(#N)C.O>[CH3:36][O:35][C:34]1[C:3](=[O:2])[C:4]([CH3:41])=[C:5]([CH2:6][C:7]2[CH:25]=[CH:24][C:10]([C:11]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)=[O:12])=[C:9]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:8]=2)[C:32](=[O:39])[C:33]=1[O:37][CH3:38]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 21919124N-[4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoyl]-4-trifluoromethylaniline

Product 1

HCID 21919202HCID 21919202, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoyl]-4-trifluoromethylaniline (55 mg, 0.0971 mmol) was dissolved in a mixed solvent of acetonitrile (3 ml) and water (1 ml), then CAN (157 mg, 0.2918 mmol) was added thereto at room temperature and the mixture was stirred for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5) to give the title compound (10 mg, 0.0186 mmol, 19%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-30c3997a34c74a358a49a586528fe18e
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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