6-Chloronicotinic acid → Ethyl 6-chloronicotinate

HRID 2258079Notes

Reaction equation

HRID 2258079 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH2:11](C(CC)(CC)C([O-])([O-])[O-])[CH3:12]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH3:12])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 792226-Chloronicotinic acidHCID 21875354Triethylorthoaceate

Product 1

HCID 2799611Ethyl 6-chloronicotinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a slurry of 6-chloronicotinic acid (5.0 g, 31.73 mmol) in anhydrous toluene (35 ml), was added dropwise with stirring triethylorthoacetate (15.45 g, 95.2 mmol). The mixture was warmed to reflux for two hours, allowed to cool to ambient temperature, and then the resultant solution was washed with saturated NaHCO3 solution (50 ml). The organic phase was dried (MgSO4) and the solvent removed in vacuo to afford the titled compound as a clear, colorless oil (5.43 g, 29.27 mmol, 92.3% yield).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for two hours
  3. washthe resultant solution was washed with saturated NaHCO3 solution (50 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-52dd8de3b76f41dd98728c69ff10a975
Source dataset
uspto-grants-1997_08
Patent number
US05659042

Reaction notes

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