Ethanol → 1-Isopropyl-5,6-Dimethyl-2-oxo-1,2-Dihydropyridine-3-Carboxylic Acid

HRID 1809354Notes

Reaction equation

HRID 1809354 reaction equation
[CH:1]([N:4]1[C:9]([CH3:10])=[C:8]([CH3:11])[CH:7]=C(C#N)[C:5]1=[O:14])([CH3:3])[CH3:2].[OH-:15].[K+].[CH2:17]([OH:19])[CH3:18]>O>[CH:1]([N:4]1[C:9]([CH3:10])=[C:8]([CH3:11])[CH:7]=[C:18]([C:17]([OH:15])=[O:19])[C:5]1=[O:14])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 592550651-Isopropyl-5,6-Dimethyl-2-oxo-1,2-Dihydropyridine-3-Carbonitrile

Product 1

HCID 592550501-Isopropyl-5,6-Dimethyl-2-oxo-1,2-Dihydropyridine-3-Carboxylic AcidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-isopropyl-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile as prepared in 3(1) (840 mg, 4.42 mmol), potassium hydroxide (1.84 g, 32.7 mmol), ethanol (12 mL) and water (3 mL) was refluxed for 16 h. After cooling, the mixture was concentrated in vacuo. The aqueous residue was diluted with water (80 mL), washed with ethyl acetate (80 mL), and acidified with 2N hydrochloric acid aqueous solution (pH˜5) at 0° C. The aqueous suspension was extracted with dichloromethane (50 mL×3). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give 838 mg (91%) of the title compound as a white solid.

Workup

  1. temperaturewas refluxed for 16 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe aqueous residue was diluted with water (80 mL)
  5. washwashed with ethyl acetate (80 mL)
  6. customacidified with 2N hydrochloric acid aqueous solution (pH˜5) at 0° C
  7. extractionThe aqueous suspension was extracted with dichloromethane (50 mL×3)
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43207e29823f4d398902a1d8a2e44715
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

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