Hydrochloric Acid → 2-Chloro-5-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 15980Notes

Reaction equation

HRID 15980 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](Cl)[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-:13].[Na+].Cl>>[Cl:1][C:2]1[NH:10][C:9](=[O:13])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27336592,6-Dichloro-5-fluoronicotinic acid

Product 1

HCID 534406372-Chloro-5-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylic acidYield 47%

Conditions

Temperature
0 °C

Procedure

A mixture of 2,6-dichloro-5-fluoronicotinic acid (15.00 g, 71.43 mmol, Lancaster Synthesis) and 2 N NaOH (178.6 ml, 357.2 mmol) was stirred at reflux for 2 hours and then at room temperature for 16 hours. The reaction mixture was cooled to 0° C. and acidified with 12 N HCl (32.74 ml, 392.9 mmol). The mixture was cooled for 30 minutes in an ice bath, the solid filtered and washed with H2O. The isolated solid was slurried in warm EtOH, filtered and then washed with warm EtOH. The solids were collected and dried under vacuum overnight to yield the desired product (6.4 g, 47%) as a beige solid.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was cooled for 30 minutes in an ice bath
  3. filtrationthe solid filtered
  4. washwashed with H2O
  5. filtrationfiltered
  6. washwashed with warm EtOH
  7. customThe solids were collected
  8. customdried under vacuum overnight

Sources & evidence

ORD record
ord-000c19cc64f04597b118f1eee5df84b7
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Reaction notes

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