Phosphoric Acid → 3-phenylpyridine-2-carboxylic Acid

HRID 1099195Notes

Reaction equation

HRID 1099195 reaction equation
[C:1]1([C:7]2[C:8]([C:13]([O:15]C)=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].P(=O)(O)(O)O>C(O)C.O>[C:1]1([C:7]2[C:8]([C:13]([OH:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 14797Potassium HydroxideHCID 11063767Methyl 3-phenylpicolinate

Product 1

HCID 27627893-phenylpyridine-2-carboxylic AcidYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-phenylpyridine-2-carboxylate (61.0 g, 286 mmol) in absolute ethanol was added potassium hydroxide (32.0 g, 572 mmol). After stirring at 50° C. for 2 h, the reaction mixture was cooled and adjusted to pH ˜7.5 with 1M phosphoric acid. The mixture was diluted with water (1 L) and extracted with EtOAc (2×600 ml). The organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo to yield 3-phenylpyridine-2-carboxylic acid as a solid (54.7 g).

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with EtOAc (2×600 ml)
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63ddd22df8d6470085bdb09419a4e982
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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