Ethanol → Ethyl 2-Chloro-6-methylisonicotinate

HRID 1908741Notes

Reaction equation

HRID 1908741 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[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]([CH3:11])[N:10]=[C:2]([Cl:1])[CH:3]=1)[CH3:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 22625009Ethyl 2-Chloro-6-methylisonicotinate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-chloro-6-methyl-isonicotinic acid (15.5 g, 90.3 mmol) in ethanol (200 mL) and H2SO4 (0.5 mL) is stirred at 75° C. for 24 h. The solvent is evaporated and the residue is dissolved in EA (200 mL). The solution is washed with sat. aq. NaHCO3-solution (70 mL) and water (70 mL), dried over MgSO4, filtered, concentrated and dried under HV to give 2-chloro-6-methyl-isonicotinic acid ethyl ester (16.3 g) as a pink powder; LC-MS: tR=0.92 min; [M+1]+=200.17.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in EA (200 mL)
  3. washThe solution is washed with sat. aq. NaHCO3-solution (70 mL) and water (70 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under HV

Sources & evidence

ORD record
ord-4e0166569d39405193b4740606abcf08
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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