Sodium Hydroxide → 6-Methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid

HRID 559819Notes

Reaction equation

HRID 559819 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:8](=[O:20])[C:7]([C:21]([O:23]CC)=[O:22])=[CH:6][C:5]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CO.O>[CH3:3][C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[C:8](=[O:20])[C:7]([C:21]([OH:23])=[O:22])=[CH:6][C:5]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66725250Ethyl 6-methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 667252216-Methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acidYield 78.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 2M sodium hydroxide solution (2.5 ml, 5.0 mmol) was added to a solution of ethyl 6-methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylate (0.85 g, 2.12 mmol) in THF (5 ml), methanol (3 ml) and water (1 ml). The reaction mixture was stirred at room temperature for 2 h and then concentrated in vacuo. Acetonitrile (3 ml) was added to the residue and the solution was acidified using TFA. The resulting solid was collected by filtration, washed with water and acetone and air dried to give the title compound as white solid (0.62 g, 78%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionAcetonitrile (3 ml) was added to the residue
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water and acetone and air
  5. customdried

Sources & evidence

ORD record
ord-1ecde97683ea4582a15b89dc3dc05a58
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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