m-Chloroperbenzoic acid → HCID 21873713, compound

HRID 1913433Notes

Reaction equation

HRID 1913433 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[O:8][CH2:9][CH2:10][O:11][C:5]2=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:1][C:2]1[N+:7]([O-:20])=[C:6]2[O:8][CH2:9][CH2:10][O:11][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 156332996-Methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

Product 1

HCID 21873713HCID 21873713, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 6-methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (19 g, 0.12 mol) in anhydrous CH2Cl2 (250 mL) was added m-CPBA (32 g, 0.15 mol) portionwise. The mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:1) to yield 6-methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 5-oxide (15.0 g, 72%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:1)

Sources & evidence

ORD record
ord-c719cb5409ab47ddaa7edcf1c5aa1156
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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