Methanol → HCID 68154716, compound

HRID 1847612Notes

Reaction equation

HRID 1847612 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH:6]=[C:5]([C:13]([O:15]C)=[O:14])[CH:4]=[CH:3]1.[OH-].[Li+].[CH3:19]O>O>[CH3:19][C:6]1[N:7]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[C:2](=[O:1])[CH:3]=[CH:4][C:5]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 14920282HCID 14920282, compound

Product 1

HCID 68154716HCID 68154716, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

After 680 mg (2.88 mmol) of methyl 6-oxo-1-(2-thiazolyl)-1,6-dihydro-3-pyridinecarboxylate was dissolved in 12 mL of methanol and 4 mL of water, 207 mg (8.64 mmol) of lithium hydroxide was added to the solution. Afterward, the resulting reaction solution was stirred at about 75° C. for 5 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo, and aqueous HCl was then added to the reaction solution to titrate until pH 2 was reached. The resulting solid compound was filtrated to obtain a target compound (Actual yield: 466 mg, Percent yield: 73%).

Workup

  1. customAfterward, the resulting reaction solution
  2. customthe solvent was removed in vacuo, and aqueous HCl
  3. additionwas then added to the reaction solution
  4. filtrationThe resulting solid compound was filtrated
  5. customto obtain a target compound (Actual yield: 466 mg, Percent yield: 73%)

Sources & evidence

ORD record
ord-13ba772f8c3443dfb5f942aa2224c337
Source dataset
uspto-grants-2015_02
Patent number
US08952165B2

Reaction notes

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