Hydrochloride methanol → Methyl 3-cyclopropylpyridine-2-carboxylate

HRID 2238670Notes

Reaction equation

HRID 2238670 reaction equation
[CH:1]1([C:4]2[C:5]([C:10]([OH:12])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[CH3:14]O>>[CH:1]1([C:4]2[C:5]([C:10]([O:12][CH3:14])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 686851453-Cyclopropylpicolinic acid

Product 1

HCID 68687300Methyl 3-cyclopropylpyridine-2-carboxylate

Procedure

830 mg of a hydrochloride salt of the 3-cyclopropylpyridine-2-carboxylic acid [121-3] was dissolved in 100 mL of 10% hydrochloric acid-methanol solution, and heated overnight under reflux. The reaction solution was concentrated under reduced pressure, a saturated aqueous solution of sodium hydrogen carbonate was added to the obtained residue, and was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and 363 mg of methyl 3-cyclopropylpyridine-2-carboxylate [121-4] was obtained as a white solid.

Workup

  1. temperatureheated overnight
  2. temperatureunder reflux
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additiona saturated aqueous solution of sodium hydrogen carbonate was added to the obtained residue
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe insolubles were filtered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-35cad4f5ba5e4f2885be1ebfb664c756
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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