Sodium Hydroxide → 5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl) benzoic acid

HRID 1245200Notes

Reaction equation

HRID 1245200 reaction equation
C[O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29]C)=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:11]([CH:15]=1)[C:12]([OH:14])=[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>[CH3:26][O:25][C:24]1[C:3](=[O:2])[C:4]([CH3:31])=[C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH:15]=2)[C:12]([OH:14])=[O:13])[C:22](=[O:29])[C:23]=1[O:27][CH3:28]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 180504Ceric ammonium nitrateHCID 121472825-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoic Acid

Product 1

HCID 219191745-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl) benzoic acidYield 58.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl) benzoic acid (500 mg, 1.1820 mmol) was dissolved in a mixed solvent of acetonitrile (30 ml) and water (10 ml), then CAN (1.62 g, 2.9562 mmol) was added thereto at room temperature and the mixture was stirred for 3 hour. The reaction solution was poured into water, neutralized with a 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 (10% methanol-methylene chloride) to give the title compound (270 mg, 0.6870 mmol, 58%).

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 (10% methanol-methylene chloride)

Sources & evidence

ORD record
ord-48ff064ea594429989b380f838d51602
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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