Sodium Bicarbonate → N-Methyl-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-methoxyaniline

HRID 1830375Notes

Reaction equation

HRID 1830375 reaction equation
[CH3:1][N:2]([C:11](=[O:36])[C:12]1[CH:17]=[C:16]([CH2:18][C:19]2[C:20](=[O:31])[C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[C:23](=[O:26])[C:24]=2[CH3:25])[CH:15]=[CH:14][C:13]=1[O:32]C(=O)C)[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>CO.O>[CH3:1][N:2]([C:11](=[O:36])[C:12]1[CH:17]=[C:16]([CH2:18][C:19]2[C:20](=[O:31])[C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[C:23](=[O:26])[C:24]=2[CH3:25])[CH:15]=[CH:14][C:13]=1[OH:32])[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054325N-Methyl-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline

Product 1

HCID 22054280N-Methyl-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-methoxyanilineYield 78.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-Methyl-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline (0.070 g, 0.142 mmol) was dissolved in methanol (3 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (2 ml), the solution was stirred at room temperature for 3 hours. After the completion of reaction, the reaction solution was diluted with water and then extracted with ethyl acetate. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:2) to obtain the titled compound (0.050 g, 0.111 mmol, 78%).

Workup

  1. additionafter adding
  2. customAfter the completion of reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-febff8c9d13c4fd8acfb5576b0448013
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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