Hydrogen Peroxide → HCID 53949219, compound

HRID 361628Notes

Reaction equation

HRID 361628 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH2:4][CH:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.OO.[C:18](=O)([O-])[O-:19].[K+].[K+].S(OC)(OC)(=O)=O>CO>[CH3:18][O:19][N:6]1[C:7]2[C:3](=[C:2]([CH3:1])[CH:10]=[CH:9][C:8]=2[CH3:11])[CH:4]=[C:5]1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 54118280HCID 54118280, compound

Product 1

HCID 53949219HCID 53949219, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with 1.0 g (4.9 mmol) of methyl 4,7-dimethylindoline-2-carboxylate and 64 mg (0.193 mmol) of sodium tungstate-dihydrate, and the air in the reaction system was substituted with nitrogen. After 15 ml of methanol was added and the reaction mixture was cooled to 0° C., 1.25 g of 30% aqueous hydrogen peroxide solution was added and the reaction mixture was stirred for 3 hours. Then 1.1 g of potassium carbonate and 0.68 g of dimethyl sulfate were added dropwise and the reaction mixture was stirred at 0° C. for 1 hour. The reaction mixture was added dropwise to ice water and extracted with 15 ml of ethyl acetate three times. The ethyl acetate layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crystals thus obtained were purified by silica gel column chromatography to provide 400 mg of white crystals. Yield: 36% m.p.: 90°-91° C.; 1H-NMR (300 MHz, CDCl3 /TMS; δppm): 7.16 (s, 1H), 7.00 (d, 1H), 6.82 (d, 1H), 4.11 (s, 3H), 3.94 (s, 3H), 2.68 (s, 3H), 2.48 (s,3H)

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 1 hour
  2. extractionextracted with 15 ml of ethyl acetate three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crystals thus obtained
  6. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-108124a044ef44179e654ab409ff8f3e
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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