Sodium Bicarbonate → 4-(Trifluoromethyl)pyridin-3-ol

HRID 2377577Notes

Reaction equation

HRID 2377577 reaction equation
N[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].N([O-])=[O:13].[Na+].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O.O>[F:9][C:8]([F:11])([F:10])[C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[OH:13]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27359573-Amino-4-(trifluoromethyl)pyridineHCID 23668193Sodium Nitrite

Product 1

HCID 252104974-(Trifluoromethyl)pyridin-3-olYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 2 g (12.34 mmol) of 3-amino-4-(trifluoromethyl)pyridine in 28 ml of 50% sulfuric acid is cooled to −5° C. and a solution of 1.03 g (14.8 mmol) of sodium nitrite in 10 ml of water is added slowly. The mixture is left to return to room temperature and stirring is continued for 30 min. 25 ml of concentrated sulfuric acid are then added and the reaction mixture is stirred at 100-110° C. for 2 hours. After cooling, the reaction medium is neutralized by adding saturated sodium bicarbonate solution to pH 6-7, and the mixture is extracted with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 1.92 g of the expected compound in the form of a brown powder (yield=95%).

Workup

  1. waitThe mixture is left
  2. customto return to room temperature
  3. stirringthe reaction mixture is stirred at 100-110° C. for 2 hours
  4. temperatureAfter cooling
  5. extractionthe mixture is extracted with ethyl acetate
  6. customThe organic phase obtained
  7. washis washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84a9ab0d2ebf4e5a9c52374c13510ae8
Source dataset
uspto-grants-2008_12
Patent number
US07470671B2

Reaction notes

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