Methanol → HCID 68154716, compound

HRID 918883Notes

Reaction equation

HRID 918883 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-dadd78f5ea8446dba1df2c7da090f62a
Source dataset
uspto-grants-2016_03
Patent number
US09271976B2

Reaction notes

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