Trifluoroacetic acid → HCID 54776268, compound

HRID 660232Notes

Reaction equation

HRID 660232 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:11]=[C:6]2[C:7](=[O:8])[O:9][CH2:12][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68863832HCID 68863832, compound

Product 1

HCID 54776268HCID 54776268, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of crude methyl 5-chloro-2-methylnicotinate 1-oxide (Organic letters, 2001, J, 209, 2.29 mmol) and trifluoroacetic acid (453 μL, 3.21 mmol) in dichloromethane (20 mL) was stirred at room temperature for 2 days and heated at 45° C. for 1 hour. The mixture was partitioned between sat. aqueous sodium hydrogen carbonate (50 mL) and ethyl acetate (50 mL). The organic layer was washed with brine (50 mL), dried (sodium sulfate), and evaporated. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1/1) to afford 225 mg of the title compound.

Workup

  1. temperatureheated at 45° C. for 1 hour
  2. customThe mixture was partitioned between sat. aqueous sodium hydrogen carbonate (50 mL) and ethyl acetate (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-68a418057d864a70ab1567bc8413200c
Source dataset
uspto-grants-2011_12
Patent number
US08084476B2

Reaction notes

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