Methanol → HCID 59134404, compound

HRID 2425346Notes

Reaction equation

HRID 2425346 reaction equation
[CH3:1][C:2]1([CH3:18])[O:17][C:6]2=[CH:7][C:8]3[C:9]([CH3:16])=[CH:10][C:11]([CH3:15])=[N:12][C:13]=3[CH:14]=[C:5]2[CH:4]=[CH:3]1.ClC1C=CC=[C:22]([C:26]([O:28]O)=[O:27])C=1.CO.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:26]([O:28][CH2:15][C:11]1[CH:10]=[C:9]([CH3:16])[C:8]2[CH:7]=[C:6]3[O:17][C:2]([CH3:18])([CH3:1])[CH:3]=[CH:4][C:5]3=[CH:14][C:13]=2[N:12]=1)(=[O:27])[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 59134423HCID 59134423, compound

Product 1

HCID 59134404HCID 59134404, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline (3.0 g, 12.5 mmol) in chloroform (30.0 mL), a solution of m-chloroperbenzoic acid (4.76 g, 27.6 mmol) in chloroform (12 mL)-methanol (3 mL) was added dropwise at room temperature, and the resulting mixture was stirred at room temperature for 30 minutes. Upon the completion of the reaction, sodium thiosulfate aqueous solution was added to the reaction solution, and it was extracted. The resulting organic phase was washed with sodium hydrogencarbonate and then with sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, acetic anhydride (12 mL) was added to the residue, and the resulting mixture was stirred at 150° C. for 1 hour. Upon the completion of the reaction, acetic anhydride was distilled off, the residue was neutralized with sodium carbonate aqueous solution, extracted with chloroform, and the resulting organic phase was washed with sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by medium pressure column chromatography (hexane/ethyl acetate=2/1) and the aimed product was obtained (yield: 64%).

Workup

  1. additionwas added to the reaction solution, and it
  2. extractionwas extracted
  3. washThe resulting organic phase was washed with sodium hydrogencarbonate
  4. dry with materialwith sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent, acetic anhydride (12 mL)
  6. additionwas added to the residue
  7. stirringthe resulting mixture was stirred at 150° C. for 1 hour
  8. customUpon the completion of the reaction, acetic anhydride
  9. distillationwas distilled off
  10. extractionextracted with chloroform
  11. washthe resulting organic phase was washed with sodium chloride aqueous solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationAfter distilling off the solvent
  14. customthe residue was purified by medium pressure column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-35f5295217e847b5b0f0e5419765040f
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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