Hydrochloric Acid → 1-Benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

HRID 1967873Notes

Reaction equation

HRID 1967873 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])=[CH:10][C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]1=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23144210Benzyl 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 181796161-Benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Benzyl 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylate (1.08 g, 3.38 mmol) obtained in Step 2 was dissolved in a mixed solvent of methanol (7 mL) and water (7 mL), and sodium hydroxide (0.680 g, 16.9 mmol) was added thereto, followed by stirring under heating and reflux for 30 minutes. The reaction mixture was poured into water (50 mL), and 10% hydrochloric acid was added thereto to adjust the pH to 4.5, followed by stirring at room temperature for 1 hour. The precipitated solid was collected by filtration to afford the entitled Compound w (151 mg, 20%) as a white solid.

Workup

  1. additionwas added
  2. temperatureunder heating
  3. temperaturereflux for 30 minutes
  4. additionwas added
  5. stirringby stirring at room temperature for 1 hour
  6. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-209b1d918f9542ceaaef08d43d70d3e1
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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