Sodium Hydroxide → 2,6-Diethyl-1,4-dihydro-4-oxopyridine-3-carboxylic acid

HRID 2254695Notes

Reaction equation

HRID 2254695 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[NH:6][C:7]([CH2:16][CH3:17])=[CH:8][C:9](=[O:15])[C:10]=1[C:11]([O:13]C)=[O:12])[CH3:4]>CO>[CH2:3]([C:5]1[NH:6][C:7]([CH2:16][CH3:17])=[CH:8][C:9](=[O:15])[C:10]=1[C:11]([OH:13])=[O:12])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 149504762,6-diethyl-4-hydroxy-3-Pyridinecarboxylic acid methyl ester

Product 1

HCID 149504772,6-Diethyl-1,4-dihydro-4-oxopyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M Sodium hydroxide (30 ml) was added to a solution of methyl 2,6-diethyl-1,4-dihydro-4-oxopyridine-3-carboxylate (obtained as described in European Patent Application No. 453210) in methanol (60 ml) and the solution was heated under reflux for 48 hours. Volatile material was removed by evaporation and the residue was dissolved in water (50 ml). The solution was washed with ethyl acetate and acidified to pH 4 with 1M citric acid solution. The resultant precipitate was collected by filtration to give 2,6-diethyl-1,4-dihydro-4-oxopyridine-3-carboxylic acid (E) (2.1 g), m.p. 238°-240° C. (decomposition); NMR (CDCl3): 1.3(t, 6H), 2.7(q, 2H), 3.3(q, 2H), 6.45(s, 1H), 12.1(br s, 1H).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 48 hours
  3. customVolatile material was removed by evaporation
  4. dissolutionthe residue was dissolved in water (50 ml)
  5. washThe solution was washed with ethyl acetate
  6. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-51aa4428adb648c5a51159946869bc02
Source dataset
uspto-grants-1993_08
Patent number
US05236936

Reaction notes

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