Trifluoroacetic acid → 2-Chloro-3-nitro-6-picoline-N-oxide

HRID 864973Notes

Reaction equation

HRID 864973 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.FC(F)(F)C(O)=[O:15].C(OO)(=O)C>C(O)(=O)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N+:3]=1[O-:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6585Peracetic AcidHCID 12682302-Chloro-6-methyl-3-nitropyridine

Product 1

HCID 194174682-Chloro-3-nitro-6-picoline-N-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Chloro-3-nitro-6-picoline (2 g, 11.6 mmol) was added to an ice cooled mixture of trifluoroacetic acid (6 mL) and 30% peracetic acid in acetic acid (6 mL). The mixture was allowed to warm to room temperature over 30 minutes and was heated in a 60° C. oil bath for 5 hours. The mixture was partitioned between methylene chloride (100 mL) and water (50 mL). The pH was adjusted to 8 with 2.5N sodium hydroxide and the aqueous layer was extracted with more methylene chloride (2×50 mL). The combined methylene chloride layers were dried with magnesium sulfate, filtered and evaporated to give the title compound as a white solid (1.6 g).

Workup

  1. temperaturecooled
  2. temperaturewas heated in a 60° C. oil bath for 5 hours
  3. customThe mixture was partitioned between methylene chloride (100 mL) and water (50 mL)
  4. extractionthe aqueous layer was extracted with more methylene chloride (2×50 mL)
  5. dry with materialThe combined methylene chloride layers were dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ac985b201812401180dd0f5f6a5ae86b
Source dataset
uspto-grants-1996_10
Patent number
US05565445

Reaction notes

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