Sodium Bicarbonate → N-(5-Hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide

HRID 1830408Notes

Reaction equation

HRID 1830408 reaction equation
[OH:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:36])[C:12]2[CH:17]=[C:16]([CH2:18][C:19]3[C:20](=[O:31])[C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[C:23](=[O:26])[C:24]=3[CH3:25])[CH:15]=[CH:14][C:13]=2[O:32]C(=O)C)=[N:8][CH:9]=1)=[O:3].C(=O)([O-])O.[Na+]>CO.Cl>[OH:3][C:2]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:36])[C:12]2[CH:17]=[C:16]([CH2:18][C:19]3[C:20](=[O:31])[C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[C:23](=[O:26])[C:24]=3[CH3:25])[CH:15]=[CH:14][C:13]=2[OH:32])=[N:8][CH:9]=1)=[O:1]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054147N-(5-Hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide

Product 1

HCID 22054234N-(5-Hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamideYield 79.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

N-(5-Hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (0.085 g, 0.172 mmol) was dissolved in methanol (6 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 a 2N hydrochloric acid solution and the aqueous layer was rendered acidic (pH=3 to 4) 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 recrystallized from ether to obtain the titled compound (0.062 g, 0.137 mmol, 79%).

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 recrystallized from ether

Sources & evidence

ORD record
ord-ab5263d79f7648f1bce2b934a842ae37
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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