Hydrochloric Acid → 3-Cyclopropylpicolinic acid

HRID 1750486Notes

Reaction equation

HRID 1750486 reaction equation
[CH:1]1([C:4]2[C:5]([C:10]([O:12]C)=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Li+].Cl>C1COCC1.O>[CH:1]1([C:4]2[C:5]([C:10]([OH:12])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68687300Methyl 3-cyclopropylpyridine-2-carboxylate

Product 1

HCID 686851453-Cyclopropylpicolinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-cyclopropylpyridine-2-carboxylate (80 mg, 0.45 mmol) in THF (2 ml) and water (2 ml) was added lithium hydroxide (55 mg, 1.36 mmol) and the reaction mixture was refluxed for 2 hours. The reaction was then acidified to pH 2 using 1M HCl (aq) and extracted with DCM (3×50 ml). The combined organics were washed with water (30 ml), brine (30 ml), dried over sodium sulfate and concentrated in vacuo to afford the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. extractionextracted with DCM (3×50 ml)
  3. washThe combined organics were washed with water (30 ml), brine (30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-802bb63e6c1745ac80524b9fa1ec178f
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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