Water → ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate N-oxide

HRID 335144Notes

Reaction equation

HRID 335144 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]2[CH2:18][N:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][C:13]=12.O>C(Cl)Cl>[N+:12]1([O-:9])[CH:17]=[CH:16][CH:15]=[C:14]2[CH2:18][N:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][C:13]=12

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 18953634ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate

Product 1

HCID 66995055ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate N-oxideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (7.3 g, 30 mmol) was added into a solution of ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate (5 g, 26 mmol) in CH2Cl2 (200 mL) and stirred for 2 hours. The reaction was poured into water and extracted with CH2Cl2. The organic layer was washed with aqueous sodium bisulfate, NaHCO3 and brine, dried with Na2SO4, filtered and concentrated to afford the title compound (4 g, 74% yield) as a white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with aqueous sodium bisulfate, NaHCO3 and brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15ed5a4d79264b83ae2a2f7429a56439
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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