Hydrogen Peroxide → 5,6-dichloropyridine-2-carboxylic acid-N-oxide

HRID 1837436Notes

Reaction equation

HRID 1837436 reaction equation
OO.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[N:8][C:9]=1[Cl:10].[OH:14]S([O-])=O.[Na+]>FC(F)(F)C(O)=O>[Cl:3][C:4]1[C:9]([Cl:10])=[N+:8]([O-:14])[C:7]([C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 132780162-Pyridinecarboxylic acid, 5,6-dichloro-HCID 23665763Sodium Bisulfite

Product 1

HCID 129936895,6-dichloropyridine-2-carboxylic acid-N-oxide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

50% Hydrogen peroxide (38 g, 0.35 mol) was carefully added to a mechanically stirred mixture of trifluoroacetic acid (350 mL) and 5,6-dichloropyridine-2-carboxylic acid (56.4 g, 0.29 mol) at 79° C. After one hour, the reaction mixture was poured into 1 L of saturated aqueous NaHSO3, stirring vigorously and cooling in an ice bath. The precipitate was collected and dried to provide 5,6-dichloropyridine-2-carboxylic acid-N-oxide (62.9 g, 0.30 mol), mp 160° C.

Workup

  1. temperaturecooling in an ice bath
  2. customThe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-13e6f9fb0c974244bd1fff3fa373763a
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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