Sodium Bicarbonate → HCID 22054352, compound

HRID 1830395Notes

Reaction equation

HRID 1830395 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1.C(=O)([O-])O.[Na+]>CO.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054313HCID 22054313, compound

Product 1

HCID 22054352HCID 22054352, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(6-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 (chloroform:methanol=10:1) and then recrystallized from ether to obtain the titled compound (0.056 g, 0.126 mmol, 88%).

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 (chloroform:methanol=10:1)
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-b1a93747d38b4f51b14ac51c1d744918
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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