Sodium Hydroxide → 2-Methyl-1-{[3-(methyloxy)phenyl]methyl}-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

HRID 734761Notes

Reaction equation

HRID 734761 reaction equation
[CH3:1][C:2]1[N:3]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:4](=[O:22])[CH2:5][CH:6]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[C:7]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+]>CO>[CH3:1][C:2]1[N:3]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:4](=[O:22])[CH2:5][CH:6]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:16][CH:17]=2)[C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68828345Methyl 2-methyl-1-{[3-(methyloxy)phenyl]methyl}-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylate

Product 1

HCID 688296512-Methyl-1-{[3-(methyloxy)phenyl]methyl}-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step 1 (0.762 g, 1.76 mmol, 1.00 equiv) was dissolved in MeOH (20 mL) and NaOH (2.0 M, 3.5 mL) and the mixture was heated to reflux for 1.5 hours. The reaction was cooled to room temperature and concentrated en vacuo. The residue was dissolved in H2O and 6N HCl was added to acidify the solution to pH 1. The crystalline precipitate was isolated by filtration, washed with H2O and air dried. The residue was further dried en vacuo to provide 0.586 g (80%) of the product as an amorphous solid. MS (ES+) m/e 420 [M+H]+

Workup

  1. temperatureto reflux for 1.5 hours
  2. concentrationconcentrated en vacuo
  3. dissolutionThe residue was dissolved in H2O
  4. addition6N HCl was added
  5. customThe crystalline precipitate was isolated by filtration
  6. washwashed with H2O and air
  7. customdried
  8. customThe residue was further dried en vacuo

Sources & evidence

ORD record
ord-971ab6fa7cfb4c4fb0442adbc32df279
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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