Sodium Bicarbonate → HCID 22054307, compound

HRID 1830397Notes

Reaction equation

HRID 1830397 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[C:18](=[O:29])[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21](=[O:24])[C:22]=3[CH3:23])[CH:13]=[CH:12][C:11]=2[O:30]C(=O)C)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])O.[Na+]>CO.O>[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[C:18](=[O:29])[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21](=[O:24])[C:22]=3[CH3:23])[CH:13]=[CH:12][C:11]=2[OH:30])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054356HCID 22054356, compound

Product 1

HCID 22054307HCID 22054307, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(2-Chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (0.070 g, 0.144 mmol) was dissolved in methanol (3 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (1.5 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 (ethyl acetate:hexane=1:1) and then recrystallized from ether to obtain the titled compound (0.040 g, 0.0903 mmol, 63%).

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=1:1)
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-b6447c89da2a467b97682cdec3cac7da
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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