Hydrochloric Acid → 3-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

HRID 1744278Notes

Reaction equation

HRID 1744278 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[C:4]1[C:9]([C:10](N)=[O:11])=[CH:8][N:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-:16].[Na+].[Na+]>O>[F:2][C:3]([F:14])([F:13])[C:4]1[C:9]([C:10]([OH:16])=[O:11])=[CH:8][N:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27826434-Trifluoromethylnicotinamide

Product 1

HCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-Yield 89.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 ml of 35% concentrated hydrochloric acid (10 ml, 57 mmol) was added to 4-trifluoromethylnicotinamide (90 g, 10 mmol), and the mixture was heated under reflux for 5 hours. Water (50 ml) was added, and the mixture was adjusted to pH 3 using sodium carbonate, and then extracted with ethyl acetate twice. The organic layers were combined, dried over magnesium sulfate and then concentrated under reduced pressure to obtain 1.71 g (yield 89.7%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted with ethyl acetate twice
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cda37f95ed984053b102ea4188e17396
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

Loading…