Carbon Dioxide → 3-Fluoropyridine-4-carboxylic acid

HRID 1091348Notes

Reaction equation

HRID 1091348 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.C(NC(C)C)(C)C.[C:20](=[O:22])=[O:21].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 677943-FluoropyridineHCID 178418339Butyllithium

Product 1

HCID 3453613-Fluoropyridine-4-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoropyridine (25 g, 257 mmol) was added to a solution of butyllithium (270 mmol) and diisopropylamine (27.4 g, 271 mmol) in tetrahydrofuran (600 mL) at −78° C. After stirring for one hour, crushed dry ice was added to the solution and the solution was warmed to room temperature during one hour. Aqueous hydrogen chloride was added to the solution to acidify the solution to pH 5. The resulting precipitate was filtered and dried. The title compound (25.2 g, 179 mmol, 70%) was obtained as colorless crystal.

Workup

  1. additionwas added to the solution
  2. filtrationThe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-fb9a85fdcace456696bb7e22fcdb2813
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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