Dichloroacetic Acid → Ethyl 6-hydroxy-3-methylpicolinate

HRID 919780Notes

Reaction equation

HRID 919780 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8](Cl)[N:7]=1)=[O:5])[CH3:2].ClC(Cl)C(O)=[O:17].C([O-])(O)=O.[Na+]>O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8](=[O:17])[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6597Dichloroacetic AcidHCID 516892Sodium BicarbonateHCID 42600466Ethyl 6-chloro-3-methylpicolinate

Product 1

HCID 19349114Ethyl 6-hydroxy-3-methylpicolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloro-3-methyl-pyridine-2-carboxylic acid ethyl ester (650 mg, 3.26 mmol), dichloroacetic acid (5 mL) and water (0.5 mL) was refluxed for 1 h. After cooling to r.t., the mixture was neutralized with saturated NaHCO3 and extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give 230 mg of the title compound as a white solid. MS: (+) m/z 182.25 (M+1).

Workup

  1. temperaturewas refluxed for 1 h
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fdf52a35ab0f4aebb3166194aa64a039
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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