Hydrochloric Acid → Methyl 3-ethylpyridine-4-carboxylate

HRID 630222Notes

Reaction equation

HRID 630222 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH2:12]([Zn]CC)[CH3:13].O.Cl>O1CCOCC1>[CH2:12]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2762700Methyl 3-bromoisonicotinateHCID 178418750HCID 178418750, compound

Product 1

HCID 59589393Methyl 3-ethylpyridine-4-carboxylateYield 21.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-bromopyridine-4-carboxylate (5 g, 23.1 mmol) was dissolved in anhydrous dioxane (150 mL). A solution of diethyl zinc (18.9 mL, 20.8 mmol, 1.1 M in toluene) was added dropwise and then was added catalyst ((1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (254 mg, 347 μmol). The mixture was heated at 70° C. for 3.5 hours and then water followed with 1 N HCl was added. The mixture was extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-20% hexane/ethyl acetate to afford methyl 3-ethylpyridine-4-carboxylate (730 mg, 19% yield).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted 3 times with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 0-20% hexane/ethyl acetate

Sources & evidence

ORD record
ord-4893d5a6374547719213bd3c7fb2a9fb
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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