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

HRID 911828Notes

Reaction equation

HRID 911828 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-994d3f1bd6844b47ac1a9eb8826fe50a
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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