Sodium Hydroxide → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridyl)benzoyl]morpholine

HRID 1245219Notes

Reaction equation

HRID 1245219 reaction equation
C[O:2][C:3]1[C:4]([CH3:36])=[C:5]([C:27]([O:34]C)=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13].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+].[OH-].[Na+]>C(#N)C.O>[CH3:31][O:30][C:29]1[C:3](=[O:2])[C:4]([CH3:36])=[C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:11]([CH:20]=2)[C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])[C:27](=[O:34])[C:28]=1[O:32][CH3:33]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 180504Ceric ammonium nitrateHCID 21919144N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]morpholine

Product 1

HCID 21919200N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridyl)benzoyl]morpholineYield 63.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]morpholine (102 mg, 0.2037 mmol) was dissolved in a mixed solvent of acetonitrile (15 ml) and water (5 ml), then CAN (279 mg, 0.5091 mmol) was added thereto at room temperature and the mixture was stirred for 3 hours. The reaction solution was poured into water, neutralized with 1N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (methylene chloride:methanol=95:5) to give the title compound (60 mg, 0.1298 mmol, 63%).

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 silica gel column chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-c19ed0c8ef8846d5a3682dcf3539ef5f
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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