Ethanol → Ethyl 2-Chloro-6-methylisonicotinate

HRID 2040767Notes

Reaction equation

HRID 2040767 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].[CH3:12][CH2:13]O>S(=O)(=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 AcidCatalyst

Procedure

A solution of 2-chloro-6-methylisonicotinic acid (15.5 g, 90.3 mmol, 1 equivalent) in EtOH (200 mL) and a few drops of concentrated sulfuric acid is stirred at 75° C. for 24 h. The solvent is evaporated and the residue is dissolved in ethyl acetate (200 mL) and washed with a solution of sat. aq. NaHCO3 (70 mL) and water (2×70 mL). The org. extract is dried over MgSO4, filtered and evaporated to give 2-chloro-6-methylisonicotinic 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 ethyl acetate (200 mL)
  3. washwashed with a solution of sat. aq. NaHCO3 (70 mL) and water (2×70 mL)
  4. extractionextract
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ec3080f2cb044f4e894ec425b57dfc7b
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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