Sodium Hydroxide → 1-Isobutyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

HRID 2192484Notes

Reaction equation

HRID 2192484 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([CH3:17])[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14]C)=[O:13])=[CH:8][C:7]1=[O:16]>CO>[CH3:3][CH:4]([CH3:17])[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59214340HCID 59214340, compound

Product 1

HCID 446005741-Isobutyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2M aqueous solution of sodium hydroxide (5.38 ml, 10.75 mmol) was added to a solution of methyl 1-(2-methylpropyl)-2-oxo-1,2-dihydro-4-pyridinecarboxylate (D27; 0.45 g, 2.151 mmol) in methanol (10 ml). The mixture was stirred at room temperature for 2 hrs and then the solvent was removed under vacuum. The residue was taken up with water, neutralised with 2M HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulphate and concentrated under vacuum to give the title compound as a white solid (400 mg).

Workup

  1. customthe solvent was removed under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-80a094f04e5c448c801008136ebf029e
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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