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

HRID 1830416Notes

Reaction equation

HRID 1830416 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:33])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]3[C:17](=[O:28])[C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[C:20](=[O:23])[C:21]=3[CH3:22])[C:10]=2[O:29]C(=O)C)[CH:2]=1.C(=O)([O-])O.[Na+]>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:33])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]3[C:17](=[O:28])[C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[C:20](=[O:23])[C:21]=3[CH3:22])[C:10]=2[OH:29])[CH:2]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054224HCID 22054224, compound

Product 1

HCID 22054239N-(Pyridin-3-yl)-3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamideYield 64.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(Pyridin-3-yl)-3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (0.060 g, 0.133 mmol) was dissolved in methanol (2 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (1.5 ml), the solution was stirred at room temperature for 2 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 (ethyl acetate:hexane=4:1) and then recrystallized from methanol to obtain the titled compound (0.035 g, 0.0857 mmol, 64%).

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 (ethyl acetate:hexane=4:1)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-68ca9de41fc64b28add183ec6d934763
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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