Lithium hydroxide, monohydrate → HCID 68492502, compound

HRID 658361Notes

Reaction equation

HRID 658361 reaction equation
[CH3:1][N:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[C:4]([C:10]([O:12]C)=[O:11])[C:3]1=[O:14].O.[OH-].[Li+]>C1COCC1.O>[CH3:1][N:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[C:4]([C:10]([OH:12])=[O:11])[C:3]1=[O:14]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68492766HCID 68492766, compound

Product 1

HCID 68492502HCID 68492502, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1,2-dihydro-1-methyl-6-methylthio-2-oxopyridine-3-carboxylate (2.1 g, 9.8 mmol) and lithium hydroxide monohydrate (0.50 g, 12 mmol) were dissolved in a mixed solvent of THF (30 mL) and water (2 mL), and stirred for a day at room temperature. The reaction mixture was concentrated under reduced pressure. To thus obtained residue, a mixed solution of aqueous saturated sodium bicarbonate and ethyl acetate was added, and then liquid separation and extraction were subjected. The obtained liquid layer was added with diluted hydrochloric acid to give a pH of 3 to 4, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain 1.6 g of a desired product (yield: 82%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo thus obtained residue, a mixed solution of aqueous saturated sodium bicarbonate and ethyl acetate was added
  3. customliquid separation and extraction
  4. additionThe obtained liquid layer was added with diluted hydrochloric acid
  5. customto give a pH of 3 to 4
  6. extractionextracted with chloroform
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a5ebbd7ddc2143e9926820b0d3991cf3
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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