Hydrochloric Acid → HCID 118598586, compound

HRID 1050364Notes

Reaction equation

HRID 1050364 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](C(OC)=O)[CH:3]=1.OO.NC(N)=[O:16].FC(F)(F)[C:20]([O:22][C:23](=[O:28])[C:24](F)(F)F)=O.Cl>ClCCl>[CH3:4][C:3]1[C:24]([C:23]([O:22][CH3:20])=[O:28])=[N+:5]([O-:16])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 46311149Methyl 4-fluoropyridine-2-carboxylate

Product 1

HCID 118598586HCID 118598586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-fluoropicolinate (2, 1 g, 6.45 mmol) in dichloromethane (30 mL) is added urea hydrogen peroxide (1.27 g, 13.54 mmol) and trifluoroacetic anhydride (1.79 mL, 12.9 mmol). The reaction is stirred at room temperature for 2 h. The resulting mixture is pour into 0.5 M hydrochloric acid and extracted with dichloromethane. The organic layer is washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The crude is purified via flash chromatography to afford methyl 4-fluoro-2-(methoxycarbonyl)pyridine 1-oxide (3).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer is washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude is purified via flash chromatography

Sources & evidence

ORD record
ord-d2f6dd8838264e709ed51b842c805886
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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