Hydrogen Peroxide → HCID 21194567, compound

HRID 564985Notes

Reaction equation

HRID 564985 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([O:16][CH3:17])=[O:15])#[N:2].C(=O)([O-])[O-:19].[Na+].[Na+].OO.S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([O:16][CH3:17])=[O:15])(=[O:19])[NH2:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 14956184HCID 14956184, compound

Product 1

HCID 21194567HCID 21194567, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.12 g (13.7 mmol) of methyl 1-(2-cyanoethyl)-2-indolecarboxylate, 30 ml of 10% sodium carbonate solution, 30 ml of 30% hydrogen peroxide and 100 ml of acetone was stirred at room temperature for 4 hours. Next, the reaction mixture was cooled to 0° C. and 10% sodium sulfite solution was added dropwise to decompose an excess of the peroxide. The most of acetone in the reaction mixture was then distilled off and the concentrate was extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2.30 g (68%) of methyl 1-(2-carbamoylethyl)-2-indolecarboxylate.

Workup

  1. temperatureNext, the reaction mixture was cooled to 0° C.
  2. distillationThe most of acetone in the reaction mixture was then distilled off
  3. extractionthe concentrate was extracted three times with ethyl acetate
  4. washThe combined extracts were washed with saturated sodium chloride solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d69fe6d6d5e94a02bd1cc3bc78acde4e
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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