Hydrochloric Acid → 2-oxo-1-(o-tolyl)-1,2-Dihydropyridine-3-carboxylic acid

HRID 2095796Notes

Reaction equation

HRID 2095796 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16]C)=[O:15])[C:9]1=[O:18].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[C:9]1=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58158571Methyl 1-(2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 581585982-oxo-1-(o-tolyl)-1,2-Dihydropyridine-3-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (9 mL) of methyl 1-(2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (880 mg, 3.62 mmol) in methanol was added 1N aqueous sodium hydroxide solution (5 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was adjusted to pH<7 with 1N hydrochloric acid and concentrated under reduced pressure. The precipitate was collected by filtration and washed with water to give the title compound (704 mg, 85%) as yellow crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-b852c9d83c844046b7e3b55f98249303
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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