Sodium Bicarbonate → HCID 22054341, compound

HRID 1830333Notes

Reaction equation

HRID 1830333 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:35])[C:5]([CH3:34])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:30]C(=O)C)=[C:17]([CH:29]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4](=[O:35])[C:5]([CH3:34])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:30])=[C:17]([CH:29]=2)[C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054310HCID 22054310, compound

Product 1

HCID 22054341HCID 22054341, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-cyanoaniline (0.100 g, 0.211 mmol) was dissolved in methanol (6 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (3 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) and then recrystallized from ether to obtain the titled compound (0.063 g, 0.146 mmol, 69%).

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)
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-8cf6c6f0c58e4e119a6fd324278c1e3a
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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