Sodium Hydroxide → 4-(2,4-Difluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid

HRID 734744Notes

Reaction equation

HRID 734744 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]1[C:17]([O:19]C)=[O:18].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]1[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2854420HCID 2854420, compound

Product 1

HCID 220489194-(2,4-Difluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acidYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product from Step 1 (600 mg, 2.13 mmol) was dissolved in methanol (15 mL), and NaOH (5 mL, 2.5 M) was added. This reaction mixture was heated to 60° C. for 18 h. The reaction mixture was concentrated, and then poured into EtOAc (20 mL) and water (5 mL). The aqueous layer was acidified to pH<3 by adding 6N HCl solution, and then extracted with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was triturated with 5% ether/hexanes to afford the title compound (287 mg, 50%). MS (ES+) m/e 268 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into EtOAc (20 mL) and water (5 mL)
  3. additionby adding 6N HCl solution
  4. extractionextracted with EtOAc (50 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was triturated with 5% ether/hexanes

Sources & evidence

ORD record
ord-b871665281de4879a832f9195dd998d8
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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