Lithium Hydroxide → 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid

HRID 1020014Notes

Reaction equation

HRID 1020014 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[C:5]([C:14]([O:16]C)=[O:15])[CH:4]=[CH:3]1.[OH-].[Li+]>CO.O>[O:1]=[C:2]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[C:5]([C:14]([OH:16])=[O:15])[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11989075Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 119888126-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acidYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

After 750 mg (3.27 mmol) of methyl 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylate was dissolved in 9 mL of methanol and 3 mL of water, 235 mg (9.81 mmol) of lithium hydroxide was added to the solution. Afterward, the resulting reaction solution was stirred at about 50° C. for about 5 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo, followed by addition of aqueous HCl to titrate a pH of the reaction product to pH 2. After filtration of the resulting solid compound (Actual yield: 470 mg, Percent yield: 67%), the resulting compound was used without purification.

Workup

  1. customAfterward, the resulting reaction solution
  2. customthe solvent was removed in vacuo
  3. additionfollowed by addition of aqueous HCl
  4. filtrationAfter filtration of the resulting solid compound (Actual yield: 470 mg, Percent yield: 67%)
  5. customthe resulting compound was used without purification

Sources & evidence

ORD record
ord-8b9ecc189bc7488eb1c7455747eba401
Source dataset
uspto-grants-2014_05
Patent number
US08716309B2

Reaction notes

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