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

HRID 2204200Notes

Reaction equation

HRID 2204200 reaction equation
[CH:1]([N:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12]C)=[O:11])=[CH:6][C:5]1=[O:14])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O>[CH:1]([N:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][C:5]1=[O:14])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58550769HCID 58550769, compound

Product 1

HCID 446007331-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 1-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylate (225 mg) was added NaOH (550 μL of 25% w/w, 4.3 mmol) and water (0.6 mL). The mixture was rapidly stirred and heated at 50° C. for 1 h. The mixture was cooled, acidified to pH 2 with 6N aq. HCl and the solids collected, rinsing with water and ACN (2×). The solid was dried in vacuo to give 1-isopropyl-2-oxo-pyridine-4-carboxylic acid as a white solid. ESI-MS m/z calc 181.2, found 182.3 (M−1)−. Retention time: 0.86 minutes (3 min run).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solids collected
  3. washrinsing with water and ACN (2×)
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-33f591a88cee43cbbb7bc571620c896b
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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