Ethanol → Ethyl chloronicotinate

HRID 1984292Notes

Reaction equation

HRID 1984292 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:11](O)[CH3:12].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:11][CH3:12])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 762582-Chloronicotinic acid

Product 1

HCID 2796614Ethyl chloronicotinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloronicotinic acid (5.90 g, 37.5 mmol), ethanol (120 mL), toluene (35 mL) and 98% sulfuric acid (2 mL) were heated together under reflux for 48 hours. After evaporation of the ethanol and toluene, the residue was dissolved in water, neutralized with sodium bicarbonate, and extracted with chloroform. The organic layer was dried through MgSO4, and then the solvent was evaporated to give a dark-brown oil-like residue, which was purified by flash chromatography using a gradient of 10-20% hexane/ethyl acetate as the eluant to give ethyl 2-chloronicotinate (4.60 g) as a light-brown oil.

Workup

  1. temperatureunder reflux for 48 hours
  2. customAfter evaporation of the ethanol and toluene
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried through MgSO4
  6. customthe solvent was evaporated
  7. customto give a dark-brown oil-like residue, which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-165a683159ea414cb042f12c3702742f
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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