Sodium Hydroxide → 5-(4-Fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid

HRID 1046024Notes

Reaction equation

HRID 1046024 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:20])[C:10]([C:15]([O:17]CC)=[O:16])=[CH:11][N:12]([CH3:14])[CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:20])[C:10]([C:15]([OH:17])=[O:16])=[CH:11][N:12]([CH3:14])[CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68009264Ethyl 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 602042125-(4-Fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylate (1.1 g, 4 mmol) and NaOH (1.6 g, 40 mmol) in water (25 mL) was stirred at RT overnight. The mixture was extracted with EtOAc (2×25 mL) to remove impurities. The aqueous pH was adjusted to pH 1-2 with 37% HCl. The resulting precipitate was collected by filtration and dried under vacuum to afford 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid (810 mg, 81.9% yield). 1H-NMR (400 MHz, CDCl3): δ 15.76 (s, 1H), 8.49 (d, J=2.4 Hz, 1H), 7.58 (m, 3H), 7.14 (t, J=8.8 Hz, 2H), 3.92 (s, 3H).

Workup

  1. extractionThe mixture was extracted with EtOAc (2×25 mL)
  2. customto remove impurities
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8bb23c2dcdf24d03aba7371911f56fa1
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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