Hydrogen Peroxide → HCID 59464117, compound

HRID 1713877Notes

Reaction equation

HRID 1713877 reaction equation
OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:6].[Cl:16][C:17]1[N:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[Cl:16][C:17]1[N+:22]([O-:6])=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 53419528Methyl 2-(6-chloropyridin-3-yl)acetate

Product 1

HCID 59464117HCID 59464117, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Hydrogen peroxide (0.409 mL of a 30% aqueous solution, 3.6 mmol) was added slowly to a stirred solution of trifluoroacetic anhydride (0.915 mL, 6.55 mmol) in DCM (5 mL) with heating under reflux. After 30 min, methyl (6-chloropyridin-3-yl)acetate (Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2004), 43B(4), 864) (608 mg, 3.28 mmol) was added as a solution in DCM (5 mL). The reaction mixture was stirred under reflux for 1 h and then allowed to cool with stirring for 16 h. Solid potassium carbonate was added until there was no more effervescence then the mixture was filtered, concentrated by evaporation and the resultant oil was triturated with Et2O to give the title compound (291 mg, 44%) as a solid; 1H NMR δ 3.64 (s, 3H), 3.79 (s, 2H), 7.30 (d, 1H), 7.75 (d, 1H), 8.45 (s, 1H); MS m/e MH+ 202.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureunder reflux for 1 h
  4. temperatureto cool
  5. stirringwith stirring for 16 h
  6. filtrationthe mixture was filtered
  7. concentrationconcentrated by evaporation
  8. customthe resultant oil was triturated with Et2O

Sources & evidence

ORD record
ord-97c365d1229a4cd0bc4dab6cd48547a3
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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