m-Chloroperbenzoic acid → 4-Methyl-5-oxido-[1,3]dioxolo[4,5-c]pyridin-5-ium

HRID 1647170Notes

Reaction equation

HRID 1647170 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[OH:12].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][N+:3]=1[O-:12]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 199264514-Methyl-[1,3]dioxolo[4,5-c]pyridine

Product 1

HCID 199264794-Methyl-5-oxido-[1,3]dioxolo[4,5-c]pyridin-5-ium

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the methylene chloride solution of 2-methyl-3,4-methylenedioxypyridine from example I 21 sodium hydrogen carbonate (1M, 50 ml) and MCPBA (4 g, 70%) were added. The mixture was stirred at ambient temperature for 15 min whereupon the excess of MCPBA was destroyed with addition of sodium thiosulphate (1 g). The organic phase was separated and the aqueous phase was extracted with methylene chloride (3×50 ml). The collected organic phases were concentrated under reduced pressure and chromatographed on silica (CH2Cl2 /MeOH, 90:10). Yield: 120 mg (7,8%) of the title compound.

Workup

  1. customwas destroyed with addition of sodium thiosulphate (1 g)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with methylene chloride (3×50 ml)
  4. concentrationThe collected organic phases were concentrated under reduced pressure
  5. customchromatographed on silica (CH2Cl2 /MeOH, 90:10)

Sources & evidence

ORD record
ord-919326a2a7f34a9ba3ad64fc9709fe5c
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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