Sodium Bicarbonate → HCID 178493900, compound

HRID 1830420Notes

Reaction equation

HRID 1830420 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:38])[C:5]([CH3:37])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:33]C(=O)C)=[C:17]([CH:32]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:31]=[CH:30][NH:29][N:28]=3)=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.ClCCl.O>[CH3:1][O:2][C:3]1[C:4](=[O:38])[C:5]([CH3:37])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:33])=[C:17]([CH:32]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:31]=[CH:30][NH:29][N:28]=3)=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 178493899N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(1H-pyrazol-3-yl)aniline

Product 1

HCID 178493900HCID 178493900, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(1H-pyrazol-3-yl)aniline (0.090 g, 0.175 mmol) was dissolved in a mixed solvent of methanol (2 ml) and dichloromethane (1 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 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 a mixed solvent of ethyl acetate and hexane (1:1) to obtain the titled compound (0.049 g, 0.104 mmol, 59%).

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 a mixed solvent of ethyl acetate and hexane (1:1)

Sources & evidence

ORD record
ord-a308d6bef5964410b4c6f437421a4249
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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