Hydrochloric Acid → 3-Chloro-5-(trifluoromethyl)pyridin-2-ol

HRID 464130

Reaction equation

HRID 464130 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[OH-:13].[K+].Cl>C(O)(C)(C)C>[Cl:8][C:7]1[C:2](=[O:13])[NH:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 7254363-Chloro-5-(trifluoromethyl)pyridin-2-olYield 75.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4.5 g of 2,3-dichloro-5-trifluoromethylpyridine was added to a solution of 2.7 g of potassium hydroxide dissolved in 40 ml of t-butanol, and the mixture was reacted at the reflux temperature for one hour while stirring. After completion of the reaction, the reaction product was allowed to cool and made acidic with concentrated hydrochloric acid. The contents were concentrated under reduced pressure to obtain a solid which was then purified to obtain 3.1 g of the titled compound having a melting point of 165° to 166° C.

Workup

  1. customthe mixture was reacted at the reflux temperature for one hour
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. concentrationThe contents were concentrated under reduced pressure
  5. customto obtain a solid which
  6. customwas then purified

Sources & evidence

ORD record
ord-3a6e9ed31a844b1ba572167156dce05f
Source dataset
uspto-grants-1985_10
Patent number
US04546191

Linked notes

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