Potassium Hydroxide → 3,5-Dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid

HRID 1501281Notes

Reaction equation

HRID 1501281 reaction equation
[C:1]([N:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]([O:18]CC)=[O:17])=[C:11]([CH3:21])[C:10]1=[O:22])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH3:25]O.O>>[CH3:21][C:11]1[C:10](=[O:22])[N:9]([CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:25])[CH:14]=[C:13]([CH3:15])[C:12]=1[C:16]([OH:18])=[O:17]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 22242641Methanol--water (1/1)HCID 89585151Ethyl 1-benzoyl-3,5-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 895851503,5-Dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acidYield 7.3%

Procedure

To the solution of ethyl 1-benzoyl-3,5-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxylate (1.06 g, 3.54 mmol) in methanol/H2O (40 mL, 1:1) was added KOH (0.79 g, 14.16 mmol). The mixture was refluxed overnight. Then the mixture was concentrated under vacuum, diluted with water (5 mL) and acidified with 1 N HCl to pH=2. The mixture was extracted with ethyl acetate. The extractions were combined, dried over Na2SO4, and concentrated to give a residue 3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid as a white solid. (70 mg, yield 7.3%) LRMS (M+H+) m/z: calcd 271.31. found 272.1. The residue was used in the next step.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThen the mixture was concentrated under vacuum
  3. additiondiluted with water (5 mL)
  4. extractionThe mixture was extracted with ethyl acetate
  5. extractionThe extractions
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7f98cd14af0745368e516e43d54aacc8
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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