Hydrochloric Acid → 5,6-Diphenyl-pyridine-2-carboxylic acid

HRID 12565

Reaction equation

HRID 12565 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19]([O:21]CC)=[O:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].Cl>CCO>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19]([OH:21])=[O:20])=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14789610Ethyl 5,6-diphenylpyridine-2-carboxylate2×

Product 1

HCID 214715265,6-Diphenyl-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 40 mg, 0.13 mmol) and LiOH (1N, 1 ml) in EtOH (2 ml) was stirred at room temperature overnight. The mixture was acidified with 10% HCl, then extracted with EtOAc. The organic layer was washed with water, and brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo, and the residue was purified by silica gel chromatography (20-80% Ethyl acetate in hexane) to give title compound as a solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe filtered solvent was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography (20-80% Ethyl acetate in hexane)

Sources & evidence

ORD record
ord-43af859442634bd7bb2952e0d4381809
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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