Hydrochloric Acid → 5-[(2,2,2-Trifluoroethoxy)methyl]-2-pyridinecarboxylic acid

HRID 341534Notes

Reaction equation

HRID 341534 reaction equation
[OH-:1].[K+].[F:3][C:4]([F:17])([F:16])[CH2:5][O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]#N)=[N:12][CH:13]=1.Cl.[OH2:19]>CCO>[F:3][C:4]([F:17])([F:16])[CH2:5][O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([OH:19])=[O:1])=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 668029555-[(2,2,2-Trifluoroethoxy)methyl]pyridine-2-carbonitrile2×

Product 1

HCID 668032965-[(2,2,2-Trifluoroethoxy)methyl]-2-pyridinecarboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Powdered potassium hydroxide (0.331 g, 5.90 mmol) was dissolved in EtOH (2 mL) and added to 5-[(2,2,2-trifluoroethoxy)methyl]pyridine-2-carbonitrile (Intermediate 226, 0.255 g, 1.18 mmol). The mixture was heated to 110 C for 16 h. After cooling the residue was dissolved in water (3 mL), acidified to pH 1 by adding 10% aq. hydrochloric acid and extracted with EtOAc (3×20 mL). The combined organic layers were dried over sodium sulfate and concentrated to afford the title compound as a brown gum (0.252 g, 91%), which was used in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=236 Found: m/z=236, Rt=0.83 min (82%).

Workup

  1. temperatureThe mixture was heated to 110 C for 16 h
  2. temperatureAfter cooling the residue
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a17ac023ea8c4e2e95371cf3b6f21b97
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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