Ethanol → 2,6-Dichloro-isonicotinic acid ethyl ester

HRID 2047267Notes

Reaction equation

HRID 2047267 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].[CH2:12](O)[CH3:13]>OS(O)(=O)=O>[CH2:12]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:11])[N:10]=[C:2]([Cl:1])[CH:3]=1)[CH3:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 948232,6-Dichloro-isonicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,6-dichloroisonicotinic acid (20.0 g, 104 mmol) in ethanol (250 mL) and H2SO4 (5 mL) is stirred at 80° C. for 28 h. The solvent is removed in vacuo and the residue is dissolved in EA, washed with sat. aq. NaHCO3 solution and water, dried over MgSO4, filtered and evaporated to give 2,6-dichloroisonicotinic acid ethyl ester (17.7 g) as a brownish solid; LC-MS: tR=1.31 min.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in EA
  3. washwashed with sat. aq. NaHCO3 solution and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1e4adcd5273b464aa8af739e3d317282
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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