Sodium Hydroxide → 2-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid

HRID 734670Notes

Reaction equation

HRID 734670 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17]([O:19]C)=[O:18])=[CH:5][CH:4]=1.[OH-].[Na+]>CO.O>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2854419HCID 2854419, compound

Product 1

HCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Step 1 (1.00 g, 3.34 mmol, 1.00 equiv) was dissolved in MeOH (11 mL). Following addition of 2.5N NaOH (4 mL), the reaction mixture was heated to reflux for 8 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed again with 1N NaOH. The aqueous phases were combined and acidified to pH˜1 with 5N HCl, and extracted twice with ethyl acetate. The combined organic extracts were washed with satd. NaCl, dried over Na2SO4, and filtered. The filtrate was concentrated en vacuo and azeotroped several times with hexanes. The resulting white solid was triturated with Et2O to afford 146 mg (15%) of the acid as an off-white solid. MS (ES+) m/e 266 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 8 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed again with 1N NaOH
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organic extracts were washed with satd
  7. dry with materialNaCl, dried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated en vacuo
  10. customazeotroped several times with hexanes
  11. customThe resulting white solid was triturated with Et2O

Sources & evidence

ORD record
ord-b0f8f09855544a9089207f679097f169
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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