Hydrochloric Acid → 5-(4-Fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

HRID 1472611Notes

Reaction equation

HRID 1472611 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([O:16]CC)=[O:15])=[CH:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([OH:16])=[O:15])=[CH:11][NH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 602042075-(4-Fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acidYield 100%

Procedure

A suspension of Example A7 (0.750 g, 2.87 mmol) in 3M NaOH (7.5 mL, 22.50 mmol) was heated at 100° C. for 1.5 h. The mixture was cooled to RT, acidified to pH 2 with 3M HCl and the resulting solid was collected via filtration and dried to afford 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (669 mg, 100%) as a white solid. MS (ESI) m/z: 234.1 (M+H+).

Workup

  1. filtrationthe resulting solid was collected via filtration
  2. customdried

Sources & evidence

ORD record
ord-b7527fb3ab4844598377d60e38f606f8
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

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