Hydrochloric Acid → Methyl 3,5-difluoropyridine-2-carboxylate

HRID 1177153Notes

Reaction equation

HRID 1177153 reaction equation
[F:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[CH3:13]O>O1CCOCC1>[CH3:13][O:10][C:9]([C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][N:4]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 27832623,5-Difluoropyridine-2-carboxylic acid

Product 1

HCID 46311137Methyl 3,5-difluoropyridine-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

3,5-Difluoropicolinic acid (1.40 g, 8.78 mmol) was dissolved in 30 mL MeOH and 0.5 mL 4.0 M HCl in 1,4-dioxane. The mixture was heated at 60° C. for 1.5 h and concentrated. Saturated aqueous NaHCO3 was added. The mixture was extracted with EtOAc, dried over Na2SO4, and concentrated to give a yellow solid (1.30 g, 86% yield). 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J=2.27 Hz, 1 H) 7.28-7.47 (m, 1 H) 4.03 (s, 3 H); LCMS for C7H5F2NO2 m/z 174.00 (M+H+).

Workup

  1. concentrationconcentrated
  2. additionSaturated aqueous NaHCO3 was added
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0076171aae949b4a14ccd1f797f90a3
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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