Sodium Hydroxide → 5-Bromo-3-fluoropyridine-2-carboxylic acid

HRID 873320Notes

Reaction equation

HRID 873320 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8](N)=[O:9])=[N:6][CH:7]=1.[OH-:12].[Na+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8]([OH:12])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 210758715-Bromo-3-fluoropyridine-2-carboxamide

Product 1

HCID 210758725-Bromo-3-fluoropyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Bromo-3-fluoropicolinamide (1.44 g, 6.5 mmol) was stirred at 120° C. in conc. HCl (17 mL) for 1.5 h. The mixture was cooled in an ice bath and the pH adjusted to pH 5 with NaOH solution (48%, aq.). The mixture was extracted with 40% MeOH in DCM, dried using a phase separator and concentrated in vacuo to give a brown powder.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionThe mixture was extracted with 40% MeOH in DCM
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give a brown powder

Sources & evidence

ORD record
ord-2fddfdba1d38444eadd3b8888a19eba1
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

Loading…