m-Chloroperbenzoic acid → 2-Methyl-5-nitro-1-oxo-1lambda~5~-pyridine

HRID 1680460Notes

Reaction equation

HRID 1680460 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[N+:8]([O-:19])[C:7]([CH3:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27945522-Methyl-5-nitropyridine

Product 1

HCID 127053092-Methyl-5-nitro-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g of 5-nitro-2-picoline are dissolved in 60 ml of methylene chloride and 4.05 g (20 m mole) of 85% m-chloroperbenzoic acid are added while stirring at room temperature. Stirring is continued overnight and the mixture is washed twice with aqueous sodium bicarbonate and then with water. It is dried, evaporated and the residue crystallized from acetonitrile, to yield the 5-nitro-2-picoline-N-oxide melting at 149°-153°.

Workup

  1. stirringStirring
  2. washthe mixture is washed twice with aqueous sodium bicarbonate
  3. customIt is dried
  4. customevaporated
  5. customthe residue crystallized from acetonitrile

Sources & evidence

ORD record
ord-5c2c3dd16b1a40a7a718ab15c4821040
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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